Bis-arylphosphate ester antagonists of platelet activating factor

ABSTRACT

The invention is novel compounds of the formula: ##STR1## which are antagonists of platelet activating factor.

BACKGROUND OF THE INVENTION

Platelet Activating Factor (PAF),1-0-hexadecyl/octadecyl-2-acetyl-sn-glyceryl-3-phosphorylcholine, is anether lipid produced by a variety of different cell types. Recentstudies [Snyder, F., Ann. Rep. Med. Chem., 17, 243 (1982); Pinckard, R.N., et. al., J. Adv. Inflammation Res., 4, 147 (1982); O'Flaherty, J.T., et. al., Clin. Rev. Allergy, 1, 353 (1983); Vargaftig, B. B., et.al., J. Trends. Pharmacol. Sci., 4, 341 (1983)] have shown PAF to be animportant mediator of allergic disease. Included among the physiologicalprocesses in which PAF is implicated are aggregation of platelets,inflammation, smooth muscle contraction, pain and edema. PAF isimplicated in asthma, respiratory distress syndrome, lung edema andother inflammatory and cardiovascular diseases.

The compounds of the present invention have proven to be specificinhibitors of the biological effects of PAF and are consequently usefulfor the treatment of asthma, anaphylactic and septic shock, psoriasis,bowel necrosis, adult respiratory distress syndrome, transplantrejection, thrombosis, stroke, cardiac anaphylaxis and cancer.

BRIEF SUMMARY OF THE INVENTION

The compounds of the present invention are represented by the Formula I.##STR2## wherein: (A) X is a phenyl or naphthyl ring optionallysubstituted in any position with one or more substituents (i) --R₂,wherein R₂ is C₁ -C₂₅ alkyl, C₁ -C₂₅ alkenyl, C₁ -C₂₅ alkoxy, C₁ -C₂₅alkenyloxy, C₁ -C₂₅ thioalkyl, phenyl, phenoxy, substituted phenyl orsubstituted phenoxy wherein the substituents are C₁ -C₂₀ alkyl, C₁ -C₂₀alkoxy, halogen or trifluoromethyl; (ii) hydrogen, halogen,trifluoromethyl, cyano, or nitro; (iii) --CO₂ R₃, --CONHR₃, --CHO,--OCONHR₃, or --NHCOR₃ wherein R₃ is C₁ -C₂₅ alkyl, C₁ -C₂₅ alkenyl,phenyl, or substituted phenyl, wherein the substituents are C₁ -C₂₀alkyl, C₁ -C₂₀ alkoxy, halogen, or trifluoromethyl; (B) R₁ representsone or more substituents of the aromatic ring which may be in anyposition and is C₁ -C₅ alkyl, C₁ -C₅ alkoxy or halogen.

--CH₂ --Y represents a single substituent of the aromatic ring which mayoccupy any position wherein Y is a mono or bicyclic aromatic heterocyclewith 5-7 membered rings containing at least one nitrogen atom which isbonded to the methylene group and optionally one or more other nitrogenor sulfur atoms; a preferred embodiment is compounds of formula I,above, wherein Y is ##STR3## wherein R₄ represents one or moresubstituents of the heterocyclic ring which may occupy and non-heteroatom position and is C₁ -C₅ alkyl, C₁ -C₅ alkoxy, hydrogen or halogen;the moiety R₅ is C₁ -C₅ alkyl or hydrogen. (C) n is the integer 0 or 1.

DETAILED DESCRIPTION OF THE INVENTION

The preparation of compounds of this invention encompassed by FormulasIA-C is described hereinbelow in Flowsheet A, wherein n, X, R₁ and R₅are described hereinabove. The moieties --CH₂ --J and --CH₂ --Y'represent substituents of the aromatic ring which are meta or para tothe phosphate group wherein J is a leaving group such as the halogenschlorine or bromine and Y' is a nitrogen containing heterocycle whichcan be ##STR4## wherein R₄ and R₅ are as described hereinabove.

According to the sequence of reactions outlined in Flowchart A, thephenol or alcohol 2 is treated with an equivalent of the phosphorusreagent 3 in the presence of a base such as triethylamine in an inertsolvent such as carbon tetrachloride to give, after hydrolysis of theresulting intermediate in a buffered solvent system such astetrahydrofuran-water-sodium acetate, the phosphate 4. The reaction of 4with a large excess of a nitrogen containing heterocycle in an inertsolvent such as toluene at 50°-150° C. gives the compounds of thisinvention represented by formula IA. These compounds are obtained asinternal salts except when A is an imidazole moiety.

In those cases where the compounds contain an imidazole ring (FormulaIB), the imidazole moiety can be further alkylated with an excess ofalkyl halide by heating in an inert solvent such as toluene to give theinternal salts IC. ##STR5##

The preparation of compounds of this invention encompassed by formulasID-IF is described hereinbelow in Flowchart B wherein R₄, Y', X, R₁, andR₅, and J are as defined hereinabove.

According to the sequence of reactions outlined in Flowchart B, thephenol 2 is treated with an equivalent of the phosphorus reagent 5 inthe presence of a base such as triethylamine in an inert solvent such ascarbon tetrachloride to give the cyclic phosphate 6. The reaction of 6with a large excess of a nitrogen containing heterocycle in an inertsolvent such as toluene at 50°-150° C. gives the compounds of thisinvention represented by formula ID. These compounds are obtained asinternal salts except when Y' is an imidazole moiety. In those caseswhere the compounds contain an imidazole ring (formula IE), theimidazole moiety can be further alkylated with an excess of alkyl halideby heating in an inert solvent such as toluene to give the internalsalts IF. ##STR6##

The phosphorous reagents represented by formulas 7a and 7b needed toprepare some of the compounds of this invention are prepared asdescribed hereinbelow in Flowsheet C and in copending application Ser.No. 316,721 filed Mar. 3, 1989 and U.S. Pat. No. 4,762,942 (1988)wherein R₁ is as defined hereinabove and J is chlorine or bromine.

According to the reaction outlined in Flowsheet C, the phenols 8a or 8bare reacted with phosphorous oxychloride and at least one equivalent ofan amine base such as triethylamine in an inert solvent such as carbontetrachloride to give the phosphorous reagents 7a and 7b. ##STR7##

The cyclic phosphorous reagents represented by formula 9 needed toprepare some of the compounds of this invention are prepared asdescribed hereinbelow in Flowsheet D wherein R₁ is as definedhereinabove.

According to the reactions outlined in Flowsheet D, the hydroxy phenol10 is treated with an equivalent of phosphorous trichloride in an inertsolvent such as ether in the presence of at least two equivalents ofpyridine to give compound 11. Oxidation of 11 with a dry stream ofoxygen in benzene then furnishes the phosphorous reagent 9. ##STR8##

The substituted phenols and hydroxy naphthalenes of Formula 12 needed toprepare the compounds of this invention can be prepared as described inthe following U.S. Pat. Nos.: 4,697,031; 4,699,990 and 4,640,913 and asdescribed hereinbelow in Flowsheet E, wherein R₆ represents one or moresubstituents which may occupy any position and are selected from thegroup consisting of hydrogen, --R₂, trifluoromethyl, and fluorinewherein R₂ is as described hereinabove, and R₇ is C₁ -C₂₅ alkyl or C₁-C₂₅ alkenyl. J' is chlorine, bromine or iodine.

According to the sequence of reactions outlined in Flowsheet E, asubstituted bromo anisol 10 is reacted with magnesium in tetrahydrofuranto form the Grignard reagent which in turn is reacted with an alkylhalide in the presence of Li₂ CuCl₄. The resulting methyl ether 11 iscleaved to the desired phenol using boron tribromide in an inert solventsuch as methylene chloride. An identical sequence of reaction can beapplied to furnish substituted hydroxy naphthalenes needed to preparesome of the compounds of this invention. ##STR9##

The substituted phenols and hydroxy naphthalenes of Formula 14 needed toprepare the compounds of this invention can be prepared as described inthe following U.S. Pat. Nos.: 4,697,031; 4,699,990 and 4,640,913, in thefollowing patent application Ser. No. 679,792, and as describedhereinbelow in Flowsheet F wherein R₂ and J' are as hereinabove definedand R₇ is C₁ -C₂₅ alkyl and C₁ -C₂₅ alkenyl. According to the sequenceof reactions shown in Flowsheet F, treatment of the dihydroxy compound13 with sodium hydride in an inert solvent such as dimethylformamide inthe presence of an alkyl halide produces the monoalkylated product 14which can readily be separated from the unreacted 13 and the dialkylatedproduct by a combination of distillation and chromatography. In thosecases where two isometric monoalkylated products result, they can beseparated using chromatographic procedures. An identical sequence ofreactions can be applied to the synthesis of the hydroxy naphthalenesneeded to prepare the compounds of this invention.

Some of the phenols and hydroxy naphthalenes that can be used to preparethe compounds of this invention are listed hereinbelow in Table I.##STR10##

TABLE 1

2-dodecyloxyphenol

2-dodecyloxy-3-chlorophenol

2-dodecyloxy-3-methoxyphenol

2-dodecyloxy-4-chlorophenol

2-dodecyloxy-4-nitrophenol

2-dodecyloxy-4-carbomethoxyphenol

2-dodecyloxy-5-methylphenol

2-dodecyloxy-5-chlorophenol

2-dodecyloxy-5-t-butylphenol

2-dodecyloxy-5-methoxyphenol

2-tetradecyloxyphenol

2-tetradecyloxy-3-nitrophenol

2-tetradecyloxy-3-carbomethoxyphenol

2-tetradecyloxy-4-methylphenol

2-tetradecyloxy-4-t-butylphenol

2-tetradecyloxy-4-carbomethoxyphenol

2-tetradecyloxy-4-methoxyphenol

2-tetradecyloxy-5-methylphenol

2-tetradecyloxy-5-t-butylphenol

2-tetradecyloxy-5-nitrophenol

2-tetradecyloxy-5-carbomethoxyphenol

2-hexadecyloxyphenol

2-hexadecyloxy-3-chlorophenol

2-hexadecyloxy-3-methoxyphenol

2-hexadecyloxy-4-methylphenol

2-hexadecyloxy-4-chlorophenol

2-hexadecyloxy-4-nitrophenol

2-hexadecyloxy-4-methoxyphenol

2-hexadecyloxy-5-chlorophenol

2-hexadecyloxy-5-methoxyphenol

3-dodecyloxyphenol

3-dodecyloxy-2-methylphenol

3-dodecyloxy-2-chlorophenol

3-dodecyloxy-2-nitrophenol

3-dodecyloxy-2-carbomethoxyphenol

3-dodecyloxy-2-methoxyphenol

3-dodecyloxy-4-methylphenol

3-dodecyloxy-4-chlorophenol

3-dodecyloxy-4-t-butylphenol

3-dodecyloxy-4-methoxyphenol

3-dodecyloxy-5-methylphenol

3-dodecyloxy-5-trifluoromethylphenol

3-dodecyloxy-5-cyanophenol

3-dodecyloxy-5-pentylphenol

3-dodecyloxy-3-methoxy-5-pentadecylphenol

3-dodecyloxy-5-methoxyphenol

3-tetradecyloxyphenol

3-tetradecyloxy-2-methylphenol

3-tetradecyloxy-2-nitrophenol

3-tetradecyloxy-2-carbomethoxyphenol

3-tetradecyloxy-2-methoxyphenol

3-tetradecyloxy-4,6-dichlorophenol

3-tetradecyloxy-4-bromophenol

3-tetradecyloxy-4-n-propylphenol

3-decyloxy-4,6-di-n-hexylphenol

3-tetradecyloxy-5-chlorophenol

3-hexadecyloxyphenol

4-dodecyloxyphenol

4-dodecyloxy-2-methylphenol

4-dodecyloxy-2-chlorophenol

4-dodecyloxy-2-t-butylphenol

4-dodecyloxy-2,5-di-t-butylphenol

5-dodecyloxy-2,4-di-t-butylphenol

4-dodecyloxy-2-carbomethoxyphenol

4-dodecyloxy-3-methylphenol

4-dodecyloxy-3-chlorophenol

4-dodecyloxy-3-t-butylphenol

4-dodecyloxy-3-nitrophenol

4-dodecyloxy-3-carbomethoxyphenol

4-tetradecyloxyphenol

4-tetradecyloxy-2-chlorophenol

4-tetradecyloxy-2-t-butylphenol

4-tetradecyloxy-2-nitrophenol

4-tetradecyloxy-3-methylphenol

4-tetradecyloxy-3-chlorophenol

4-tetradecyloxy-3-t-butylphenol

4-tetradecyloxy-3-nitrophenol

4-hexadecyloxyphenol

4-hexadecyloxy-2-methylphenol

4-hexadecyloxy-2-chlorophenol

4-hexadecyloxy-3-methylphenol

4-hexadecyloxy-3-chlorophenol

5-dodecyloxy-1-naphthalenol

7-dodecyloxy-2-naphthalenol

4-dodecyloxy-1-naphthalenol

6-dodecyloxy-2-naphthalenol

4-tetradecyloxy-2,5-dichlorophenol

The compounds of this invention were tested for pharmacological activityas described in the following tests.

PLATELET ACTIVATING FACTOR ANTAGONISM IN VITRO

Test compounds were evaluated as PAF receptor antagonists in vitro bymeasuring inhibition of PAF (platelet activating factor) inducedplatelet aggregation. Platelet aggregation was measured by amodification of the method described in A. Wissner, et. al., J. Med.Chem., 27, 1174, 1984.

Approximately 120-240 ml of blood were collected by cardiac puncturefrom unanesthetized male New Zealand White rabbits (Whaley's Summit ViewFarms, Belvedere, N.J.) with the use of 3.2% sodium citrateanticoagulant (1 part of citrate/10 parts of blood). All syringes andpipets were plastic. The blood was gently mixed and immediatelycentrifuged at 800 rpm for 10-15 minutes at room temperature to recoverthe platelet rich plasma (PRP). Platelet poor plasma (PPP) was preparedby centrifuging PRP at 2800 rpm for 10 minutes at room temperature.

Dilutions (1:3000) of PRP in Isoton® diluent were made and plateletcounts were determined on a Coulter Thrombocounter which wasstandardized with platelet reference standards (Interscience PlateletControl, Portland, Oreg.). PRP platelet counts were adjusted toapproximately 400,000-500,000 platelets/μl by the addition of PPP.

L-PAF was obtained from Calbiochem. A stock solution of 1-2 E-3M wasprepared in 10% ethanol in water or 100% methanol and serial workingdilutions were made using phosphate buffered saline (PBS). 1-2 E-3Mstock solutions of test compounds were prepared in 100% methanol andserially diluted in PBS. All solutions were made up in plastic tubes,stored on ice and protected from heat and light. Solutions were preparedfresh or frozen at -20° C. and used within 48 hours.

Incubation mixtures consisted of 400 μl PRP, 50 μl of PBS diluent ortest compound and 50 μl of PAF agonist. More specifically, 400 μl of PRPwas stabilized in a cuvette for 1-2 minutes at 37° C. in theaggregometer to achieve a stable baseline, then 50 μl of PBS or testcompound, was added and incubated for 5 minutes before addition of thechallenge concentration of PAF (final concentration of 5E-8M or 1E-7M,as determined from the dose response curve for PAF for that experiment).Aggregation was monitored for 5 minutes. Samples containing testcompound or diluent were run simultaneously for comparison. Testcompounds were initially evaluated at a screening concentration of1E-5M. Those producing ≧50% inhibition of the magnitude of aggregationwere then reevaluated in a dose response fashion (final concentrations1E-8M to 5E-5M) and IC₅₀ values were determined from the dose responsecurve.

The recording equipment consisted of a dual channel Chronologaggregometer connected to a dual channel 10 MV full scale deflectionOmniscribe chart recorder (Houston Instruments). The chart recorder wascalibrated daily with the use of a suspension of Bio-Rad latex beads(S-X 12 400 mesh) which had a density slightly greater than rabbit PRP.The bead suspension was used to set the 0% light transmission mark andclear water was used to set the 100% light transmission mark. Theselimits defined a full scale deflection. The aggregation traces wereanalyzed by a digitizing method (C. Kohler and B. Zoltan, J. Pharm.Methods, 12, 113, 1984) with x, y coordinate data stored in a computerfile. A suitable program computed parameters of interest such as themagnitude of aggregation.

In some experiments, washed rabbit platelets were used instead of rabbitPRP. Washed platelet suspensions were prepared as follows. Rabbit PRPwas centrifuged at 2800 rpm for 10 minutes to obtain PPP and a plateletpellet. The pellet was gently suspended and washed in calcium free,albumin free Tyrode's buffer, pH 6.3. The suspension was recentrifugedand the washed pellet was resuspended in normal Tyrodes' buffer (withcalcium, but albumin free), pH 7.4. Platelet counts were adjusted to500,000 platelets/μl. The challenge concentration of PAF used for washedplatelet experiments was 5E-9M.

In some experiments, human PRP was used instead of rabbit PRP. Bloodfrom healthy volunteers was collected in Vacutainers® containing the Nacitrate diluent and processed in a manner similar to rabbit blood toobtain the PRP. For these experiments, the challenge concentration ofPAF was 1E-6M.

The results of tests on representative compounds of this inventionappear in Tables III, IV, V.

                  TABLE III                                                       ______________________________________                                        Inhibition of PAF-Induced Aggregation in Rabbit                               Platelet Rich Plasma                                                          Compound                 IC.sub.50 (M)                                        ______________________________________                                        3-[[3-[[[3-(hexadecyloxy)phenoxy]                                                                      2.13E-6(4)                                           hydroxyphosphinyl]oxy]phenyl]                                                 methyl]thiazolium, hydroxide,                                                 inner salt                                                                    3-[[3-[[[3-(hexadecyloxy)-2-methyl-                                                                    2.65E-6(3)                                           phenoxy]hydroxyphosphinyl]oxy]phenyl]                                         methyl]thiazolium, hydroxide,                                                 inner salt                                                                    1-[[3-[[[3-(hexadecyloxy)phenoxy]                                                                      1.54E-5(1)                                           hydroxyphosphinyl]oxy]phenyl]                                                 methyl]pyridinium, hydroxide,                                                 inner salt                                                                    1-[[3-[[[3-(hexadecyloxy)phenoxy]                                                                      2.18E-5(1)                                           hydroxyphosphinyl]oxy]phenyl]                                                 methyl]quinolinium, hydroxide,                                                inner salt                                                                    3-[[3-[[[3-(dodecyloxy)phenoxy]                                                                        5.28E-5(2)                                           hydroxyphosphinyl]oxy]phenyl]                                                 methyl]thiazolium, hydroxide,                                                 inner salt                                                                    3-[[3-[[3-[4-(hexadecyloxy)                                                                            3.28E-6(2)                                           phenoxy]hydroxyphosphinyl]oxy]                                                phenyl]methyl]thiazolium,                                                     hydroxide, inner salt                                                         3-[[3-[[hydroxy]-2-(tetra-                                                                             5.75E-5(1)                                           decyloxy)phenoxy)phosphinyl]-                                                 oxy]phenyl]methyl]thiazolium,                                                 hydroxide, inner salt                                                         3-[[3-[[hydroxy(3-tetradecyl-                                                                          1.88E-5(2)                                           phenoxy)phosphinyl]oxy]phenyl]                                                methyl]thiazolium, hydroxide,                                                 inner salt                                                                    3-[[3-[[hydroxy[2-methoxy-3-                                                                           7.50E-6(3)                                           (tetradecyloxy)phenoxy]phos-                                                  phinyl]oxy]phenyl]methyl]-                                                    thiazolium, hydroxide, inner salt                                             1-[[3-[[hydroxy[2-methoxy-3-                                                                           1.65E-4(2)                                           (tetradecyloxy)phenoxy]phos-                                                  phinyl]oxy]phenyl]methyl]-                                                    pyridinium, hydroxide, inner salt                                             3-[[3-[[hydroxy[[3-(tetradecyl-                                                                        4.22E-6(2)                                           oxy)phenyl]methoxy]phosphinyl]                                                oxy]phenyl]methyl]thiazolium,                                                 hydroxide, inner salt                                                         1-[[3-[[hydroxy[2-methoxy-3-                                                                           8.0E-6(2)                                            (tetradecyloxy)phenoxy]phos-                                                  phinyl]oxy]phenyl]methyl]-                                                    quinolinium, hydroxide, inner salt                                            2-[[3-[[hydroxy[2-methoxy-3-                                                                           2.0E-5(2)                                            (tetradecyloxy)phenoxy]phos-                                                  phinyl]oxy]phenyl]methyl]-                                                    isoquinolinium, hydroxide,                                                    inner salt                                                                    3-[[3-[[hydroxy[2-methoxy-3-                                                                           2.51E-6(7)                                           (tetradecyloxy)phenoxy]phos-                                                  phinyl]oxy]phenyl]methyl]-5-                                                  methyl-thiazolium, hydroxide,                                                 inner salt                                                                    3-[[2-[[[3-(hexadecyloxy)phenoxy]                                                                      6.3E-6(2)                                            hydroxyphosphinyl]oxy]phenyl]                                                 methyl]thiazolium, hydroxide,                                                 inner salt                                                                    3-[[3-[[hydroxy[3-(tetradecyl-                                                                         6.15E-6(2)                                           oxy)phenoxy]phosphinyl]oxy]                                                   phenyl]methyl]thiazolium,                                                     hydroxide, inner salt                                                         3-[[3-[[hydroxy[3-(tetradecyl-                                                                         8.82E-6(2)                                           oxy)phenoxy]phosphinyl]oxy]                                                   phenyl]methyl]-5-methyl-thia-                                                 zolium, hydroxide, inner salt                                                 3-[[3-[[[2,4-bis(1,1-dimethyl-                                                                         3.02E-5(2)                                           ethyl)-5-(dodecyloxy)phenoxy]                                                 hydroxyphosphinyl]oxy]phenyl]                                                 methyl]thiazolium, hydroxide,                                                 inner salt                                                                    3-[[3-[[[2,5-bis(1,1-dimethyl-                                                                         3.03E-7(3)                                           ethyl)-4-(dodecyloxy)phenoxy]                                                 hydroxyphosphinyl]oxy]phenyl]                                                 methyl]thiazolium, hydroxide,                                                 inner salt                                                                    1-[[3-[[[3-(hexadecyloxy)-2-                                                                           2.96E-5(2)                                           methylphenoxy]hydroxyphosphinyl]                                              oxy]phenyl]methyl]quinolinium                                                 3-[[3-[[[[7-(dodecyloxy)-2-                                                                            2.64E-5(2)                                           naphthalenyl]oxy]hydroxyphos-                                                 phinyl]oxy]phenyl]methyl]thia-                                                zolium, hydroxide, inner salt                                                 3-[[3-[[hydroxy[2-(methoxycar-                                                                         2.70E-6(2)                                           bonyl)-3-(tetradecyloxy)phenoxy]                                              phosphinyl]oxy]phenyl]methyl] -                                               thiazolium, hydroxide, inner salt                                             3-[[3-[[hydroxy[2-(methoxycar-                                                                         5.21E-7(2)                                           bonyl)-3-(tetradecyloxy)phenoxy]                                              phosphinyl]oxy]phenyl]methyl]-5-                                              methyl-thiazolium, hydroxide,                                                 inner salt                                                                    1-[[3-[[hydroxy[2-(methoxycar-                                                                         6.26E-6(2)                                           bonyl)-3-(tetradecyloxy)phenoxy]                                              phosphinyl]oxy]phenyl]methyl]-                                                quinolinium, hydroxide, inner salt                                            3-[[3-[[[2,5-bis(1,1-dimethyl-                                                                         4.12E-7(4)                                           ethyl)-4-(dodecyloxy)phenoxy]                                                 hydroxyphosphinyl]oxy]phenyl]                                                 methyl]-5-methyl-thiazolium,                                                  hydroxide, inner salt                                                         1-[[3-[[[2,5-bis(1,1-dimethyl-                                                                         1.36E-6(3)                                           ethyl)-4-(dodecyloxy)phenoxy]                                                 hydroxyphosphinyl]oxy]phenyl]                                                 methyl]quinolinium, hydroxide,                                                inner salt                                                                    1-[[3-[[[3-(dodecyloxy)-2-                                                                             2.47E-5(1)                                           methoxyphenoxy]hydroxyphos-                                                   phinyl]oxy]phenyl]methyl]-                                                    quinolinium, hydroxide, inner salt                                            3-[[3-[[[3-(dodecyloxy)-2-methoxy-                                                                     1.72E-5(1)                                           phenoxy]hydroxyphosphinyl]oxy]                                                phenyl]methyl]thiazolium,                                                     hydroxide, inner salt                                                         3-[[3-[[hydroxy[2-methyl-3-[[(octa-                                                                    3.72E-6(2)                                           decylamino)carbonyl]oxy]phenoxy]phos-                                         phinyl]oxy]phenyl]methyl]thiazolium,                                          hydroxide, inner salt                                                         3-[[3-[[hydroxy[2-methyl-3-[[octa-                                                                     1.8E-6(1)                                            decylamino)carbonyl]oxy]phenoxy]phos-                                         phinyl]oxy]phenyl]methyl]-5-methyl-                                           thiazolium, hydroxide, inner salt                                             3-[[3-[[hydroxy[4-(phenylmethoxy)                                                                      1.53E-3(1)                                           phenoxy]phosphinyl]oxy]phenyl]methyl]                                         5-methyl-thiazolium, hydroxide,                                               inner salt                                                                    ______________________________________                                         Data are in Molar IC.sub.50 values (concentration which produces 50%          inhibition) in rabbit platelet rich plasma. The challenge concentration o     1PAF (platelet activating factor) was 5E8M. Numbers in parentheses refer      to number of experiments.                                                

                  TABLE IV                                                        ______________________________________                                        Inhibition of PAF-Induced Aggregation in Washed                               Rabbit Platelets                                                              Compound                IC.sub.50 (M)*                                        ______________________________________                                        3-[[3-[[hydroxy[2-methoxy-3-                                                                          5.49E-9(1)                                            (tetradecyloxy)phenoxy]phos-                                                  phinyl]oxy]phenyl]methyl]-5-                                                  methyl-thiazolium, hydroxide,                                                 inner salt                                                                    3-[[3-[[[2,5-bis(1,1-dimethyl-                                                                        2.12E-9(2)                                            ethyl)-4-(dodecyloxy)phenoxy]                                                 hydroxyphosphinyl]oxy]phenyl]                                                 methyl]thiazolium, hydroxide,                                                 inner salt                                                                    ______________________________________                                         *Data are molar IC.sub.50 values (concentration which produces 50%            inhibition) in washed rabbit platelets. The challenge concentration of PA     was 5E9M. Numbers in parentheses refer to number of experiments.         

                  TABLE V                                                         ______________________________________                                        Inhibition of PAF-Induced Aggregation in Human                                Platelet Rich Plasma                                                          Compound                 IC.sub.50 (M)                                        ______________________________________                                        3-[[3-[[[3-(hexadecyloxy)phenoxy]                                                                      2.5E-6(1)                                            hydroxyphosphinyl]oxy]phenyl]                                                 methyl]thiazolium, hydroxide,                                                 inner salt                                                                    3-[[3-[[[3-(hexadecyloxy)-2-                                                                           1.19E-7(1)                                           methylphenoxy]hydroxyphosphinyl]                                              oxy]phenyl]methyl]thiazolium,                                                 hydroxide, inner salt                                                         3-[[3-[[hydroxy[2-methoxy-3-                                                                           2.64E-5(2)                                           (tetradecyloxy)phenoxy]phos-                                                  phinyl]oxy]phenyl]methyl]-                                                    thiazolium, hydroxide, inner salt                                             3-[[3-[[hydroxy[2-methoxy-3-                                                                           3.10E-5(2)                                           (tetradecyloxy)phenoxy]phos-                                                  phinyl]oxy]phenyl]methyl]-5-                                                  methyl-thiazolium, hydroxide,                                                 inner salt                                                                    3-[[3-[[[2,5-bis(1,1-dimethyl-                                                                         1.93E-6(1)                                           ethyl)-4-(dodecyloxy)phenoxy]                                                 hydroxyphosphinyl]oxy]phenyl]-                                                thiazolium, hydroxide, inner salt                                             1-[[3-[[[2,5-bis(1,1-dimethyl-                                                                         4.75E-5(2)                                           ethyl)-4-(dodecyloxy)phenoxy]                                                 hydroxyphosphinyl]oxy]phenyl]                                                 methyl]quinolinium, hydroxide,                                                inner salt                                                                    ______________________________________                                         Data are molar IC.sub.50 values (concentration which produces 50%             inhibition) in human platelet rich plasma. Numbers in parentheses refer t     numbers of experiments.                                                  

IN VIVO TESTS FOR PAF ANTAGONISM A. Guinea Pig Vascular Permeability(Skin Lesion) Model

PAF produces a rapid increase in capillary permeability and intradermalinjection of PAF causes leakage of plasma proteins into theextracellular space. If these proteins are previously tagged with Evan'sblue dye, a blue spot develops in the skin. A PAF antagonist will reducethe leakage and reduce the size of the spot. Specificity of the PAFantagonist can be determined by also checking the response to otheragonists such as histamine.

The initial in vivo test uses coinjection of test compound and PAFagonist in the guinea pig skin model. The following protocol describesthe coinjection methodology.

Hartley strain guinea pigs (300-400 gm) were maintained with food andwater ad lib. The backs and hind feet of the animals were shaved 1 daybefore use. PAF (Sigma P9525) was dissolved in saline at 500 ng/ml anddiluted 1:1 to make a 250 ng/ml solution. Histamine diphosphate (SigmaH7375) was dissolved in saline at 25 ug/ml. Test compounds weredissolved in ETOH at 10 mg/ml. The injection solutions were made bymixing 10 ul of test compound solution or ETOH into 1 ml of PAF orhistamine solution.

The guinea pigs were given 2 ml of Evan's Blue dye (0.5% w/v) in salinevia a foot vein. Immediately after, six 0.1 ml intradermal injectionswere made into the back of the guinea pig, 3 per side. The left side wasinjected with 50 ng PAF+10 ug test compound (0.1 ml of 500 ng/ml PAF+100ug/ml test compound), 25 ng PAF+10 ug test compound, and 2.5 ughistamine+10 ug test compound. The right side was injected with the samepattern of the ETOH control solutions. In addition, a separate group ofanimals received 10 ug of test compound in saline as a control fordirect test compound effects.

Twenty minutes later, the animals were killed by a blow to the head andthe skin reflected from the back. The blue lesion areas (due toincreased vascular permeability) were estimated as the product of thelongest and shortest diameters. A compound was considered active if itreduced the PAF induced lesion by 50% or more without altering ahistamine induced lesion.

Those compounds which were active by the coinjection route were examinedby intraperitoneal administration. Two protocols were used, the firstwith both PAF and histamine as agonists; the second used 6 concentrationlevels of PAF. Protocols were similar to the methods described above,except ETOH was eliminated from the solutions.

In protocol I, the PAF was administered by intradermal injections at 50,25, and 12.5 ng/site and histamine at 2, 1, and 0.5 ug/site. In protocolII, six sites were injected with PAF at 50, 25, 12.5, 6.25, 3.125, and1.56 ng/site. For each protocol, the methods were as described above. Acompound was considered active at the dose used if it significantlyreduced the PAF lesions without altering the histamine response.

B. PAF Induced Lethality in Mice

PAF given I.V. to mice causes an immediate hypotensive shock leading todeath in 1 hour or less. Compounds were given intraperitoneally or P.O.at various times before the PAF challenge. Animals alive after 2 hourswere counted and the activity of test compounds expressed as % survivalcorrected for any control (saline treated) animals which survived thePAF challenge. Results of this assay appear in Table VI.

C. Endotoxin Induced Hypotension in Rats

Rats given LPS I.V. demonstrates a profound hypotension; to the extentthat this is a PAF induced phenomena, a PAF antagonist should restorenormal blood pressure.

Bacterial cell wall lipopolysaccharide from E. coli strain 0111:B4(Sigma #L-2630) was dissolved in saline at a concentration of 3.75 mg/mland administered to rats at 15 mg/kg I.V. Test compounds were dissolvedin saline at 1 mg/ml, diluted to 10 ug/ml, and injected intraarteriallyat 1 ml/kg (10 ug/kg). Male wistar strain rats were obtained fromCharles River Labs and maintained according to ALAC standards. They wereanesthetized with 30 mg/kg pentobarbital ip with supplementation asneeded. The throat was opened, the left carotid artery was cannulatedwith PE-10 tubing and the trachea cannulated with 0.100 O.D. tubing.Ventilation was maintained by a Harvard Apparatus small animal pump at arate sufficient to nearly abolish spontaneous respiration. The meanarterial pressure was measured using a Statham PM23 transducer anddisplayed on a Grass model 7 polygraph. Endotoxin was givenintravenously or intraarterially if the tail veins had collapsed. After5 minutes, the test compound was given intraarterially since the tailveins generally collapsed after endotoxin administration.

Results are expressed as the % reversal of the fall in mean arterialpressure as shown in Table VII.

                  TABLE VI                                                        ______________________________________                                        In Vivo Data                                                                                  PAF Induced   PAF Induced                                                     Skin Lesions  Lethality.sup.(b)                               Compound        % of Control.sup.(a)                                                                        % Protection                                    ______________________________________                                        3-[[3-[[3-[4-(hexa-                                                                           60            96                                              decyloxy)phenoxy]hy-                                                          droxyphosphinyl]oxy]                                                          phenyl]methyl]thiazo-                                                         lium, hydroxide,                                                              inner salt                                                                    3-[[3-[[hydroxy[2-                                                                            75.sup.(c)    12                                              methoxy-3-(tetradecyl-                                                        oxy)phenoxy]phosphinyl]                                                       oxy]phenyl]methyl]thia-                                                       zolium, hydroxide,                                                            inner salt                                                                    3-[[3-[[hydroxy[2-                                                                            --            17                                              methoxy-3-(tetradecyl-                                                        oxy)phenoxy]phosphinyl]                                                       oxy]phenyl]methyl]-5-                                                         methylthiazolium, hy-                                                         droxide, inner salt                                                           3-[[3-[[[2,5-bis(1,1-                                                                         49.sup.(d)     27.sup.(c)                                     dimethylethyl)-4-(do-                                                         decyloxy)phenoxy]hydroxy-                                                     phosphinyl]oxy]phenyl]                                                        methyl]thiazolium, hy-                                                        droxide, inner salt                                                           3-[[3-[[hydroxy[2-                                                                            --            12                                              (methoxycarbonyl)-3-                                                          (tetradecyloxy)phenoxy]                                                       phosphinyl]oxy]phenyl]                                                        methyl]thiazolium,                                                            hydroxide, inner salt                                                         3-[[3-[[hydroxy[2-                                                                            --             0                                              (methoxycarbonyl)-3-                                                          (tetradecyloxy)phenoxy]                                                       phosphinyl]oxy]phenyl]                                                        methyl]-5-methyl-thiazol-                                                     ium hydroxide, inner salt                                                     3-[[3-[[[2,5-bis(1,1-                                                                         --            36                                              dimethylethyl)-4-(dodec-                                                      yloxy)phenoxy]hydroxy-                                                        phosphinyl]oxy]phenyl]-                                                       methyl]-5-methyl-thia-                                                        zolium, hydroxide,                                                            inner salt                                                                    ______________________________________                                         .sup.(a) % of control when 10 ug of test compound was coinjected into         guinea pig skin with PAF                                                      .sup.(b) % prevention of death when given I.P. at 10 mg/kg except where       noted corrected for control lethality                                         .sup.(c) I.P. 4 mg/kg 1 hour before PAF                                       .sup.(d) P.O. 5 mg/kg 4 hours before PAF                                      .sup.(e) P.O. 10 mg/kg 4 hours before PAF                                

                  TABLE VII                                                       ______________________________________                                        Effect of PAF Antagonist in Reversing                                         Endotoxin Induced Hypotension                                                 Reversal of LPS Induced Hypotension in anesthetized rats.                                            % Reversal of                                          Compound               Hypotension                                            ______________________________________                                        3-[[3-[[hydroxy[2-methoxy-3-(tetrade-                                                                89                                                     cyloxy)phenoxy]-phosphinyl]oxy]phenyl]-                                       methyl]thiazolium, hydroxide, inner                                           salt                                                                          3-[[3-[[hydroxy[2-methoxy-3-(tetrade-                                                                84                                                     cyloxy)phenoxy]-phosphinyl]oxy]phenyl]                                        methyl]-5-methyl-thiazolium, hydroxide,                                       inner salt                                                                    ______________________________________                                    

D. Endotoxin Induced Shock and Mortality in Mice

Endotoxin administration produces a shock state characterized byhypotension, neutropenia, thrombocytopenia and death. PAF administrationmimics the signs and symptoms of endotoxin induced shock and death andendotoxin also induces the release of PAF. Therefore, the effects ofendotoxin should be blocked with a PAF antagonist.

Male Balb/c mice (approximately 20 g) were obtained from Charles RiverLaboratories and used after a one week acclimation period. Animals wereinjected (iv or ip) with test compound at different time intervals priorto the iv or ip injection of endotoxin. Sigma E. Coli endotoxin,0111:B4, phenol extraction, catalog #L2630 was used for these studies.

The endotoxin dose was determined from doseresponse titrations andadjusted to a dose that was lethal for 90% (LD₉₀) of the mice within a24 hour period. This LD₉₀ value was approximately 50 mg/kg iv and 80mg/kg ip. The number of survivors in each group (control or treated withtest compound) was recorded after 24, 48 or 72 hours and the treatedgroups (receiving test compound and endotoxin) was compared with theuntreated, control group (receiving endotoxin only).

The test compounds, known to be PAF antagonists from in vitro plateletaggregation studies, were active in reducing 24 hour mortality whenadministered ip prior to a lethal ip injection of endotoxin (TableVIII). The test compounds (PAF antagonists) were also efficacious whenadministered iv prior to a lethal iv injection of endotoxin (Table IX).

                  TABLE VIII                                                      ______________________________________                                        Effect of PAF Antagonists on Endotoxin:                                       Induced Mortality in Mice.sup.a                                                                    24 Hour Survival                                                              (# Alive/Total)                                          Compound        Dose (mg/kg)                                                                             Treated  Control                                   ______________________________________                                        3-[[3-[[hydroxy[2-                                                                            30         12/50    4/50                                      methoxy-3-(tetradecyl-                                                        oxy)phenoxy]phosphinyl]-                                                                      10          7/30    1/30                                      oxy]phenyl]methyl]thia-                                                       zolium, hydroxide,                                                            inner salt                                                                    3-[[3-[[hydroxy[2-                                                                            40         13/50    4/50                                      methoxy-3-(tetradecyl-                                                        oxy)phenoxy]phosphinyl]-                                                      oxy]phenyl]methyl]-5-                                                         methyl-thiazolium, hy-                                                        droxide, inner salt                                                           3-[[3-[[[2,5-bis(1,1-                                                                         40          6/20    0/20                                      dimethylethyl)-4-(do-                                                                         20          6/20    0/20                                      decyloxy)phenoxy]hydroxy-                                                     phosphinyl]oxy]phenyl]-                                                                       10          4/20    0/20                                      methyl]thiazolium,                                                            hydroxide, inner salt                                                         ______________________________________                                         .sup.a Test compound or placebo was injected (IP) 2 hours prior to the IP     injection of endotoxin. The endotoxin dose used was selected to kill          90-100% of the animals. The treated group received test compound plus         endotoxin. The control group received placebo plus endotoxin.            

                  TABLE IX                                                        ______________________________________                                        Effect of PAF Antagonists on Endotoxin:                                       Induced Mortality in Mice.sup.a                                                                    Survival                                                                      After 24 hrs.                                                                 (# Alive/Total)                                          Compound        Dose (mg/kg)                                                                             Treated  Control                                   ______________________________________                                        3-[[3-[[hydroxy[2-                                                                            10          4/20    0/20                                      methoxy-3-(tetradecyl-                                                        oxy)phenoxy]phosphinyl]-                                                      oxy]phenyl]methyl]thia-                                                       zolium, hydroxide,                                                            inner salt                                                                    3-[[3-[[hydroxy[2-                                                                            20         14/40    3/40                                      methoxy-3-(tetradecyl-                                                        oxy)phenoxy]phosphinyl]-                                                      oxy]phenyl]methyl]-5-                                                         methyl-thiazolium,                                                            hydroxide, inner salt                                                         ______________________________________                                         .sup.a Test compound or placebo was injected (IP) 2 hours prior to the IP     injection of endotoxin. The endotoxin dose used was selected to kill          90-100% of the animals. The treated group received test compound plus         endotoxin. The control group received placebo plus endotoxin.            

E. Endotoxin Induced Hemorragic Lesions in Rats

Endotoxin induces an immediate, profound hemorragic lesion in the gut ofrodents.3-[[3-[[hydroxy[2-methoxy-3-(tetradecyloxy)phenoxy]phosphinyl]oxy]phenyl]methyl]-5-methyl-thiazolium,hydroxide, inner salt given IP one hour before challenge at doses as lowas 1/2 mg/kg is able to reduce or eliminate the damage produced by IVLPS. Results of this assay appear in Table X.

One of the main sites of LPS induced pathology in the rat and guinea pigis the gut, particularly the duodenum, small intestine and cecum. AfterLPS exposure hemorragic lesions develop within a few minutes and caninvolve most of the lumenal surface. The extent of these pathologies canbe quantitated histologically or by measuring the amount of plasmaproteins that have leaked into the lumen. The second method is muchfaster and can detect damage in the junctions between capillary orintestinal epithelial cells before gross lesions have developed. Hottags have shown plasma leakage after LPS challenge using radiolabeledalbumin as the probe. In our assay we have chosen to use anon-radioactive tagging method in which plasma albumin is labeled withEvan's blue dye and the lumenal leakage is determinedspectrophotometricly.

The data available now indicates that LPS acts by inducing the synthesisand release of tumor necrosis factor (TNF) which in turn causessynthesis and release of platelet activating factor (PAF). PAF seems tobe the major cytotoxic agent involved in many of the pathophysiologicchanges seen in endotoxic shock and these changes can be induced bydirect injection of PAF. Therefore a PAF antagonist ought to prevent theintestinal damage brought on by injection of LPS. We have demonstratedthat3-[[3-[[hydroxy[2-methoxy-3-(tetradecyloxy)phenoxy]phosphinyl]oxy]phenyl]methyl]-5-methyl-thiazolium,hydroxide, inner salt prevents the gut manifestations of endotoxin shockand does so at doses as low as 0.25 mg/kg in rats.

CHEMICALS

Evan's blue dye: Sigma e-2129, made as a 1% w/v solution in saline whichwas filtered and kept refrigerated.

Platelet activating factor (PAF) was obtained from Sigma, P-9525. Thisis supplied as a chloroform solution at 2 mg/ml and was diluted in thedye solution to 2.5 μg/ml.

For each experiment fresh3-[[3-[[hydroxy[2-methoxy-3-(tetradecyloxy)phenoxy]phosphinyl]oxy]phenyl]methyl]-5-methyl-thiazolium,hydroxide, inner salt was sonicated into saline.

BIOLOGICALS

Endotoxin: Lipopolysaccharide (LPS) isolated from E. coli strain 0111:b4by phenol extraction was obtained from Sigma, L-2630. LPS solutions weremade fresh for each experiment.

ANIMALS

Male Wistar rats, obtained from Charles River, weighing 160-225 gm weremaintained in accordance with ALAC standards for at least one weekbefore use.

PROTOCOLS

Food was withheld from the animals for 18 hours before the experiment toclear the intestine. The rats were dosed with3-[[3-[[hydroxy[2-methoxy-3-(tetradecyloxy)phenoxy]phosphinyl]oxy]phenyl]methyl]-5-methyl-thiazolium,hydroxide, inner salt or saline ip, 4 ml/kg, 1/2 hour before challengewith 25 or 50 mg/kg LPS in the 1% dye at 10 ml/kg. One hour after theLPS insult the animals were sacrificed and the duodenum and initial 6-7cm of the jejunum isolated. This segment was lavaged with 2 ml of normalsaline with the fluid flowing into polyethylene tubes. The lavageatefrequently contained mucous and in order to free the stained albumin thesamples were sonicated vigorously and then centrifuged to clarify thefluid. The amount of dye was determined spectrophotometrically, using aVmax microtiter plate reader using the end point mode at 600 nM.

DISCUSSION

The most obvious damage seen in examination of rodents given endotoxinis a massively swollen caecum and hemorragic lesions in the stomach andsmall intestine. Similar pathology is also seen in humans with systemicseptic shock. The relative importance of direct capillary damage by PAFvs ischemia-reperfusion damage brought on by the profound hypotensioninduced by LPS is unknown. However,3-[[3-[[hydroxy[2-methoxy-3-(tetradecyloxy)phenoxy]phosphinyl]oxy]phenyl]methyl]-5-methyl-thiazolium,hydroxide, inner salt has demonstrated very potent protection againstthe end point of gut pathophysiology. Direct observation of theintestinal tract of LPS challenge control animals and3-[[3-[[hydroxy[2-methoxy-3-(tetradecyloxy)phenoxy]phosphinyl]oxy]phenyl]methyl]-5-methyl-thiazolium,hydroxide, inner salt protected animals revealed that the protectedanimals had nearly normal appearing guts. Blind testing became difficultas virtually all the control animals had severe diarrhea while the3-[[3-[[hydroxy[2-methoxy-3-(tetradecyloxy)phenoxy]phosphinyl]oxy]phenyl]methyl]-5-methyl-thiazolium,hydroxide, inner salt animals had little or none. The overall activityof 3-[[3-[[hydroxy[2-methoxy-3-(tetradecyloxy)phenoxy]phosphinyl]oxy]phenyl]methyl]-5-methyl-thiazolium,hydroxide, inner salt was significant with activity seen at doses as lowas 1/2 mg/kg IP.

                  TABLE X                                                         ______________________________________                                        Reduction of IV LPS Induced Gut Leakage                                       By 3-[[3-[[Hydroxy[2-methoxy-3-(tetra-                                        decyloxy)phenoxy]phosphinyl]oxy]phenyl]methyl]-                               5-methyl-thiazolium, hydroxide, inner salt                                    Given IP in Rats                                                                        % of Control Leakage (K).sup.a                                                for Each Experimental Run                                                     Experiment                                                          Dose (mg/kg)                                                                              1          2         3                                            ______________________________________                                        20.         20 ± 2  19 ± 31                                             2.          10 ± 10 18 ± 24                                                                              27 ± 11                                   1.          22 ± 15                                                        0.5         15 ± 10 16 ± 9                                              0.25        36 ± 23 65 ± 15                                             0.125       24 ± 15 107 ± 27                                            ______________________________________                                         .sup.a Values are expressed as the percentage of dye leakage in control       LPS animals corrected for background leakage ± SEM. There were from 5      to 8 animals per cell in each determination. Note columns are not             necessarily the same experiment.                                              C = Dye leakage in LPS (15 mg/kg IV) challenged animals                       B = Dye leakage in animals given dye only                                     R = Dye leakage in animals given 3[[3[[hydroxy[                               2methoxy-3-(tetradecyloxy)phenoxy]phosphinyl]oxy]phenyl]methyl5-methyl-th    azolium hydroxide, inner salt                                                  ##STR11##                                                                

The active compounds of the present invention may be orallyadministered, for example, with an inert diluent, or with an assimilableedible carrier, or they may be enclosed in hard or soft shell capsules,or they may be compressed into tablets, or they may be incorporateddirectly with the food of the diet. For oral therapeutic administration,these active compounds may be incorporated with excipients and used inthe form of tablets, capsules, elixirs, suspensions, syrups and thelike. Such compositions and preparations should contain at least 0.1% ofactive compound. The percentage of the compound in these compositionsmay, of course, be varied and may conveniently be between about 2% toabout 60% of the weight of the unit. The amount of active compound insuch therapeutically useful compositions is such that a suitable dosagewill be obtained. Preferred compositions according to this invention areprepared so that an oral dosage unit contains between about 1 and 250 mgof active compound.

The tablets, capsules and the like may also contain a binder such as gumtragacanth, acacia, corn starch or gelatin; excipients such as dicalciumphosphate; a disintegrating agent such as corn starch, potato starch,alginic acid; a lubricant such as magnesium stearate; and a sweeteningagent such as sucrose, lactose or saccharin. When the dosage unit formis a capsule, it may contain, in addition to materials of the abovetype, a liquid carrier such as a fatty oil.

Various other materials may be present as coatings or to modify thephysical form of the dosage unit. For instance, tablets may be coatedwith shellac, sugar or both. A syrup or elixir may contain, in additionto active ingredient, sucrose as a sweetening agent, methyl andpropylparabens as preservatives, a dye and flavoring such as cherry ororange flavor.

These active compounds may also be administered parenterally. Solutionsor suspensions of these active compounds can be prepared in watersuitably mixed with a surfactant such as hydroxypropylcellulose.Dispersions can also be prepared in glycerol, liquid polyethyleneglycols and mixtures thereof in oils. Under ordinary conditions ofstorage and use, these preparations contain a preservative to preventthe growth of microorganisms.

The pharmaceutical forms suitable for injectable use include sterileaqueous solutions or dispersions and sterile powders for theextemporaneous preparation of sterile injectable solutions ordispersions. In all cases, the form must be sterile and must be fluid tothe extent that easy syringability exists. It must be stable under theconditions of manufacture and storage and must be preserved against thecontaminating action of microorganisms such as bacterial and fungi. Thecarrier can be a solvent or dispersion medium containing, for example,water, ethanol, polyol (e.g. glycerol, propylene glycol and liquidpolyethylene glycol), suitable mixtures thereof, and vegetable oils.

The compounds of this invention may also be administered directly to theairways in the form of an aerosol.

The invention will be further described by the following examples.

EXAMPLE 1 3-(Bromomethyl)phenyl phosphodichlorodate

A 9.1 g portion of 99% phosphorous tribromide, 10 ml of carbontetrachloride and 1.32 ml of dry pyridine in 2.5 ml of tetrahydrofuranwas reacted with 12.41 g of 4-hydroxybenzyl alcohol in 100 ml of drytetrahydrofuran containing 0.7 ml of pyridine. The intermediate4-hydroxybenzyl bromide was treated with phosphorous oxychloride, giving5.6 g of the desired compound.

EXAMPLE 2 2-Chloro-4H-1,3,2-benzodioxaphosphorin, 2-oxide

To a solution of 100 g of hydroxybenzyl alcohol and 121.69 g ofphosphorous trichloride in 1000 ml of ether at -10° C., was addeddropwise a solution of 133.81 g of pyridine in 200 ml of ether over 1.5hours. The mixture was stirred for 1.5 hours at room temperature andthen refrigerated overnight. The mixture was filtered, the solventremoved, hexane added, the mixture filtered and the solvent removed. Theresidue was distilled via a Kugelrohr (1 mm 80°-90° C.) giving 81 g of acolorless liquid. A solution of this material in benzene was stirred anddry oxygen bubbled in for 20 hours, then the benzene was removed, giving87.5 g of the desired compound as a yellow liquid.

EXAMPLE 3 3-(Hexadecyloxy)phenol

To a suspension of 29.6 g of sodium hydride in 215 ml ofN,N-dimethylformamide was added dropwise over 1.5 hours a solution of54.33 g of resorcinol in 145 ml of N,N-dimethylformamide and 72 ml oftetrahydrofuran. The resulting mixture was cooled to 0° C. and 7.4 g ofsodium iodide added followed by the dropwise addition of 155.0 g ofhexadecylbromide over 1 hour. The bath was removed and the mixturestirred at ambient temperature for 17 hours. The mixture was dilutedwith 500 ml of iced dilute hydrochloric acid, extracted with ether andfiltered. The ether layer was dried over magnesium sulfate andevaporated to an oil which was purified by chromatography on silica gelusing ethyl acetate-hexanes giving 37.2 g of the desired compound as awhite solid, m.p. 58°-59° C.

EXAMPLE 4 3-(Bromomethyl)phenyl 3-(hexadecyloxy)phenyl phosphate

To a solution of 5.0 g of 3-(hexadecyloxy)phenol in 60 ml of dry carbontetrachloride cooled in an ice bath was added a solution of 5.5 g of3-(bromomethyl)phenyl phosphodichloride in 10 ml of carbon tetrachloridein an inert atmosphere. A solution of 2.52 ml of triethylamine in 10 mlof carbon tetrachloride was rapidly added followed by cooling bathremoval and stirring overnight. Filtered the mixture throughdiatomaceous earth and evaporated to a residue which was stirred for twohours with 130 ml of tetrahydrofuran and 130 ml of 0.5M sodium acetate.The tetrahydrofuran was removed under vacuum and the aqueous residuecooled and acidified with hydrochloric acid followed by etherextraction. The organic layer was washed with saturated sodium chloride,dried with magnesium sulfate and evaporated to a viscous oil which waspurified by chromatography on magnesium silicate with chloroform and 10%methyl alcohol-chloroform giving 7.0 g of the desired compound as aglass.

EXAMPLE 53-[[3-[[[3-(Hexadecyloxy)phenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-thiazolium,hydroxide, inner salt

To a solution of 2.0 g of 3-(bromomethyl)phenyl 3-(hexadecyloxy)phenylphosphate in 15 ml of dry toluene was added 2.3 g of triazole followedby stirring at 65°-70° C. in an inert atmosphere for 18 hours. Theresidue, from solvent removal, was purified by chromatography on silicagel with methyl alcohol-chloroform then chloroformmethyl alcohol-water,triturated with ether and refrigerated giving 1.65 g of the desiredcompound as a white amorphous solid.

EXAMPLE 61-[[3-[[[3-(Hexadecyloxy)phenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-quinolinium,hydroxide

To a solution of 2.5 g of 3-(bromomethyl)phenyl3-(hexadecyloxy)phenylphosphate in 20 ml of dry toluene was added 4.43of quinoline followed by stirring in an inert atmosphere at 70° C. for18 hours. The solvent was removed in vacuo and the residue stirred with2.5 of Amberlite IR-4B resin in 50 ml of methyl alcohol for 2 hours.Filtered the mixture and removed the solvent in vacuo then columned theresidue on silica gel with methyl alcohol-chloroform and methylalcohol-chloroform-water. Triturated with ether and refrigerated giving1.61 g of the desired compound as white amorphous powder.

EXAMPLE 71-[[3-[[[3-(Hexadecyloxy)phenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-pyridinium,hydroxide inner salt

To a solution of 2.5 g of 3-(bromomethyl)phenyl 3-(hexadecyloxy)phenylphosphate in 22 ml of dry toluene was added 2.7 g of pyridine followedby stirring, in an inert atmosphere, at 70°-75° C. for 18 hours. Thesolvent was removed in vacuo and the residue stirred with 2.5 g ofAmberlite IR-4B resin in 55 ml of methyl alcohol for 2 hours. Filteredthe mixture and removed the solvent in vacuo. The residue was columnedon silica gel with methyl alcohol-chloroform and methylalcohol-chloroform-water. Triturated with ether and refrigerated giving2.1 g of the desired compound as white amorphous powder.

EXAMPLE 83-[[2-[[[3-(Hexadecyloxy)phenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-thiazolium,hydroxide, inner salt

A mixture of 4.5 g of 3-(hexadecyloxy)phenol, 2.75 g of2-chloro-4H-1,3,2-benzodioxaphosphorin, 2-oxide and 2.06 ml oftriethylamine in 60 ml of carbon tetrachloride was stirred for 18 hours.The mixture was diluted with ether, filtered and the solvent removed.The residue following solvent removal was heated in a pressure vessel(90° C.) with 10.08 g of triazole in 50 ml of toluene for 4 days. Thesolvent was removed in vacuo and the residue purified by chromatographyon silica gel with methyl alcohol-chloroform and methylalcohol-chloroform-water. Triturated with ether and refrigerated giving2.2 g of the desired compound as white powder.

EXAMPLE 9 4-(Hexadecyloxy)phenol

To a suspension of 21.79 g of hexane washed sodium hydride in 155 ml ofN,N-dimethylformamide was added dropwise over 1.5 hours a solution of40.0 g of hydroquinone in 140 ml of N,N-dimethylformamide and 55 ml oftetrahydrofuran. The resulting mixture was cooled to 0° C. and 5.45 g ofsodium iodide added, followed by the dropwise addition of 152.0 g ofhexadecylbromide over 1.25 hours. The bath was removed and the mixturestirred at ambient temperature for 17 hours. The mixture was dilutedwith ice and 500 ml of cold dilute hydrochloric acid, extracted withether and filtered. The ether layer was dried over sodium sulfate andevaporated to a syrup which was purified by chromatography on silica gelwith ethyl acetate-hexanes giving 8.0 g of the desired compound as awhite solid, m.p. 87°-88° C.

EXAMPLE 10 3-(Bromomethyl)phenyl 4-(hexadecyloxy)phenyl phosphate

To a solution of 1.0 g of 4-(hexadecyloxy)phenol in 10 ml of dry carbontetrachloride and 2 ml of ether cooled in a water bath was added asolution of 1.1 g of 3-(bromomethyl)phenyl phosphodichlorodate in 2 mlof carbon tetrachloride in an inert atmosphere. A solution of 2.4 ml oftriethylamine in 2 ml of carbon tetrachloride was rapidly added followedby cooling bath removal and stirring for 4 hours. The mixture wasfiltered through diatomaceous earth and evaporated to a residue whichwas stirred for two hours with 25 ml of tetrahydrofuran and 25 ml of0.5M sodium acetate then refrigerated overnight. The tetrahydrofuran wasremoved under vacuum and the aqueous residue cooled and acidified withhydrochloric acid followed by ether extraction. The organic layer waswashed with saturated sodium chloride, dried with magnesium sulfate andevaporated to a syrup which was purified by chromatography on magnesiumsilicate with chloroform and 10% methyl alcohol-chloroform giving 1.57 gof the desired compound as a glass.

EXAMPLE 113-[[3-[[[4-(Hexadecyloxy)phenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

To a solution of 1.5 g of 3-(bromomethyl)phenyl 4-(hexadecyloxy)phenylphosphate in 15 ml of dry toluene was added 1.8 g of thiazole followedby stirring in an inert atmosphere, at 65°-70° C. for 18 hours. Thesolvent was removed in vacuo and the residue stirred with 1.5 ofAmberlite® IR-4B resin in 40 ml of methyl alcohol for 1.5 hours. Themixture was filtered and the solvent removed in vacuo. The residue wascolumned on silica gel with methyl alcohol-chloroform and methylalcohol-chloroform-water. Triturated with ether and refrigerated giving1.18 g of the desired compound as a white amorphous powder.

EXAMPLE 12 3-(Hexadecyloxy)-2-methylphenol

To a suspension of 25.0 g of hexane washed sodium hydride in 215 ml ofN,N-dimethylformamide was added dropwise over 1.5 hours a solution of60.0 g of 2-methylresorcinol in 145 ml of N,N-dimethylformamide and 72ml of tetrahydrofuran. The resulting mixture was cooled to 0° C. and7.25 g of sodium iodide added followed by the dropwise addition of 152.0g of hexadecylbromide over 1 hour. The bath was removed and the mixturestirred at ambient temperature for 18 hours. The mixture was dilutedwith 500 ml of iced dilute hydrochloric acid, extracted with ether andfiltered. The ether layer was dried over magnesium sulfate andevaporated to an oil which was purified by chromatography on silica gelgiving 54.5 g of the desired compound as a white solid, m.p. 53°-54° C.

EXAMPLE 13 3-(Bromomethyl)phenyl 3-(hexadecyloxy)-2-methylphenylphosphate

To a solution of 5.0 g of 3-(hexadecyloxy)-2-methyl phenol in 60 ml ofdry carbon tetrachloride, cooled in an ice bath, was added a solution of5.23 g of 3-(bromomethyl)phenyl phosphodichlorodate in 10 ml of carbontetrachloride in an inert atmosphere. A solution of 2.4 ml oftriethylamine in 10 ml of carbon tetrachloride was rapidly addedfollowed by cooling bath removal and stirring overnight. Filtered themixture through diatomaceous earth and evaporated to a residue which wasstirred for two hours with 130 ml of tetrahydrofuran and 130 ml of 0.5Msodium acetate. The tetrahydrofuran was removed under vacuum and theaqueous residue cooled and acidified with hydrochloric acid followed byether extraction. The organic layer was washed with saturated sodiumchloride, dried with magnesium sulfate and evaporated to a syrup whichwas purified by chromatography on magnesium silicate with chloroform and10% methyl alcohol-chloroform giving 6.5 g of the desired compound as aglass following solvent removal.

EXAMPLE 14 3-[[3-[[[3-(Hexadecyloxy)-2-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-thiazolium, hydroxide, inner salt

To a solution of 2.3 g of 3-(bromomethyl)phenyl3-(hexadecyloxy)-2-methylphenyl phosphate in 20 ml of dry toluene wasadded 2.62 g of thiazole followed by stirring, in an inert atmosphere,at 60°-65° C. for 18 hours. The solvent was removed in vacuo and theresidue stirred with 2.3 g of Amberlite® IR-4B resin in 60 ml of methylalcohol for 2 hours. The mixture was filtered and the solvent wasremoved in vacuo. The residue was columned on silica gel with methylalcohol-chloroform and methyl alcohol-chloroform-water. Triturated withether and refrigerated giving 1.92 g of the desired compound as a whiteamorphous powder.

EXAMPLE 15 2-(Tetradecyloxy)phenol

To a mechanically stirred suspension of 29.6 g of hexane washed sodiumhydride in 215 ml of N,N-dimethylformamide was added dropwise underargon over 1.5 hours a solution of 54.33 g of catechol in 145 ml ofN,N-dimethylformamide and 72 ml of tetrahydrofuran. The resultingmixture was cooled to 0° C. and 7.4 g of sodium iodide added followed bythe dropwise addition of 144.0 g of 1-bromotetradecane over 1 hour. Thebath was removed and the mixture stirred at ambient temperature for 18hours. The mixture was diluted with 500 ml of dilute hydrochloric acid,extracted with ether and filtered. The ether layer was dried overmagnesium sulfate and evaporated to an oil which was purified bychromatography on silica gel giving 54.5 g of the desired compound as awhite solid, m.p. 53°-54° C.

EXAMPLE 16 3-(Bromomethyl)phenyl 2-(tetradecyloxy) phenyl phosphate

To a solution of 1.0 g of 2-(tetradecyloxy)phenol in 10 ml of dry carbontetrachloride cooled in a water bath was added a solution of 1.19 g of3-(bromomethyl)phenyl phosphodichlorodate in 2 ml of carbontetrachloride in an inert atmosphere. A solution of 396 mg oftriethylamine in 23 ml of carbon tetrachloride was rapidly addedfollowed by cooling bath removal and stirring for 4 hours. Filtered themixture through diatomaceous earth and evaporated to a residue which wasstirred for 1.5 hours with 25 ml of tetrahydrofuran and 25 ml of 0.5Msodium acetate. The tetrahydrofuran was removed under vacuum and theaqueous residue cooled and acidified with hydrochloric acid followed byether extraction. The organic layer was washed with saturated sodiumchloride, dried with magnesium sulfate and evaporated to a syrup whichwas purified by chromatography on magnesium silicate with chloroform and10% methyl alcohol-chloroform giving 1.75 g of the desired compound as aglass.

EXAMPLE 17 3-[[3-[[Hydroxy[2-(tetradecyloxy)phenoxy]phosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

To a solution of 1.7 g of 3-(bromomethyl)phenyl 2-(tetradecyloxy)phenylphosphate in 15 ml of dry toluene was added 2.08 g of thiazole followedby stirring, in an inert atmosphere, at 67° C. for 18 hours. The solventwas removed in vacuo after 48 hours and the residue stirred with 1.7 gof Amberlite® IR-4B resin in 50 ml of methyl alcohol for 1 hour. Themixture was filtered and the solvent removed in vacuo. The residue wascolumned on silica gel with methyl alcohol-chloroform and methylalcohol-chloroform-water. Triturated with ether and refrigerated giving1.38 g of the desired compound as a white amorphous powder.

EXAMPLE 18 3-(Tetradecyloxy)phenol

To a suspension of 29.6 g of hexanes washed sodium hydride under argonin 215 ml of N,N-dimethylformamide was added dropwise over 1.5 hours asolution of 54.33 g of resorcinol in 145 ml of N,N-dimethylformamide and72 ml of tetrahydrofuran. The resulting mixture was cooled to 0° C. and7.4 g of sodium iodide added followed by the dropwise addition of 144.0g of 1-bromotetradecane over 1 hour. The bath was allowed to melt andthe mixture stirred for 2 days. The mixture was diluted with ice and 300ml of cold dilute hydrochloric acid, extracted with ether and filtered.The ether layer was dried over magnesium sulfate and evaporated to anoil which was purified by chromatography on silica gel using ethylacetatehexanes giving 40.8 g of the desired product as a white solid,m.p. 49°-50° C.

EXAMPLE 19 3-(Bromomethyl)phenyl 3-(tetradecyloxy)phenyl phosphate

To a solution of 2.0 g of 3-(tetradecyloxy)phenol in 25 ml of dry carbontetrachloride cooled in an ice bath was added a solution of 2.43 g of3-(bromomethyl)phenyl phosphodichlorodate in 5 ml of carbontetrachloride in an inert atmosphere. A solution of 1.1 ml oftriethylamine in 5 ml of carbon tetrachloride was rapidly added followedby cooling bath removal and stirring overnight. Filtered the mixturethrough diatomaceous earth and evaporated to a residue which was stirredfor 1.5 hours with 55 ml of tetrahydrofuran and 55 ml of 0.5M sodiumacetate. The tetrahydrofuran was removed under vacuum and the aqueousresidue cooled and acidified with hydrochloric acid followed by etherextraction. The organic layer was washed with saturated sodium chloride,dried with magnesium sulfate and evaporated to a syrup which waspurified by chromatography on magnesium silicate with chloroform and 10%methyl alcohol-chloroform giving 3.0 g of the desired compound as aglass.

EXAMPLE 203-[[3-[[Hydroxy[3-(tetradecyloxy)phenoxy]phosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

To a solution of 1.5 g of 3-(bromomethyl)phenyl 3-(tetradecyloxy)phenylphosphate in 15 ml of dry toluene was added 1.84 g of thiazole followedby stirring, in an inert atmosphere, at 65° C. for 18 hours. The solventwas removed in vacuo and the residue stirred with 1.5 g of Amberlite®IR-4B resin in 40 ml of methyl alcohol for 1 hour. The mixture wasfiltered and the solvent removed in vacuo. The residue was columned onsilica gel with methyl alcohol-chloroform and methylalcohol-chloroform-water. Triturated with ether and refrigerated giving1.01 g of the desired compound as a white amorphous powder.

EXAMPLE 213-[[3-[[Hydroxy[3-(tetradecyloxy)phenoxy]phosphinyl]oxy]phenyl]methyl]-5-methyl-thiazolium,hydroxide, inner salt

To a solution of 1.5 g of 3-(bromomethyl)phenyl 3-(tetradecyloxy)phenylphosphate in 15 ml of dry toluene was added 2.14 g of 5-methylthiazolefollowed by stirring in an inert atmosphere at 65° C. for 17 hours. Thesolvent was removed in vacuo and the residue stirred with 1.5 g ofAmberlite® IR-4B resin in 40 ml of methyl alcohol for 1.5 hours. Themixture was filtered and the solvent removed in vacuo. The residue wascolumned on silica gel with methyl alcohol-chloroform and methylalcohol-chloroform-water. Triturated with ether and refrigerated giving1.06 g of the desired compound as a white amorphous powder.

EXAMPLE 22 2-Methoxy-3-(tetradecyloxy)phenol

To a suspension of 3.8 g of hexane washed sodium hydride in 25 ml ofN,N-dimethylformamide was added dropwise over 1.5 hours a solution of60.0 g of 2-methoxy resorcinol in 50 ml of N,N-dimethylformamide. Theresulting mixture was cooled to 0° C. and 1.07 g of sodium iodide addedfollowed by the dropwise addition of 19.79 g of 1-bromotetradecane over20 minutes. The bath was removed and the mixture stirred at ambienttemperature for 18 hours. The mixture was poured into dilutehydrochloric acid and extracted with ether. The ether layer was driedover magnesium sulfate and evaporated to an oil which was distilledusing a Kugelrohr apparatus and the fraction boiling at 130°-180°/0.1 mmcollected. Purification using high pressure liquid chromatography onsilica gel using hexanes-ether gave 8.7 g of the desired compound as anoil.

EXAMPLE 23 3-(Bromomethyl)phenyl 2-methoxy-3-(tetradecyloxy) phenylphosphate

To a solution of 8.0 g of 2-methoxy-3-(tetradecyloxy)phenol in 60 ml ofdry carbon tetrachloride cooled in an ice bath was added a solution of8.67 g of 3-(bromomethyl)phenyl phosphodichlorodate in 10 ml of carbontetrachloride in an inert atmosphere. A solution of 3.98 ml oftriethylamine in 10 ml of carbon tetrachloride was rapidly addedfollowed by cooling bath removal and stirring overnight. The mixture wasfiltered through diatomaceous earth and evaporated to a residue whichwas stirred for 1.5 hours with 250 ml of tetrahydrofuran and 250 ml of0.5M sodium acetate. The tetrahydrofuran was removed under vacuum andthe aqueous residue cooled and acidified with hydrochloric acid followedby ether extraction. The organic layer was washed with saturated sodiumchloride, dried with magnesium sulfate and evaporated to a syrup whichwas purified by chromatography on magnesium silicate with chloroform and10% methyl alcohol-chloroform giving 11.4 g of the desired compound asan oil.

EXAMPLE 24 3-[[3-[[Hydroxy[2-methoxy-3-(tetradecyloxy)phenoxy]phosphinyl]oxy]phenyl]methyl]-thiazolium,hydroxide inner salt

To a solution of 3.0 g of3-(bromomethyl)phenyl)-2-methoxy-3-(tetradecyloxy)phenyl phosphate in 20ml of dry toluene was added 2.62 g of thiazole followed by stirring, inan inert atmosphere, at 95° C. for 2.5 hours. The solvent was removed invacuo and the residue stirred with 2.18 g of Amberlite® IR-4B resin in50 ml of methyl alcohol for 10 minutes. The mixture was filtered and thesolvent removed in vacuo. The residue was columned on silica gel withmethyl alcohol-chloroform and methyl alcohol-chloroform-water.Triturated with ether and refrigerated giving 1.73 g of the desiredcompound as a white amorphous powder.

EXAMPLE 253-[[3-[[Hydroxy[2-methoxy-3-(tetradecyloxy)phenoxy]phosphinyl]oxy]phenyl]methyl]-5-methyl-thiazolium,hydroxide, inner salt

To a solution of 1.8 g of3-(bromomethyl)phenyl-2-methoxy-3-(tetradecyloxy)phenyl phosphate in 15ml of dry toluene was added 1.52 g of 5-methyl thiazole followed bystirring, in an inert atmosphere, at 80° C. for 5 hours. The solvent wasremoved in vacuo and the residue stirred with 5.0 g of Amberlite® IR-4Bresin in 60 ml of methyl alcohol for 1 hour. The mixture was filteredand the solvent removed in vacuo. The residue was columned on silica gelwith methyl alcohol-chloroform and methyl alcohol-chloroform-water.Triturated with ether and refrigerated giving 0.93 g of the desiredcompound as a white amorphous powder.

EXAMPLE 261-[[3-[[Hydroxy[2-methoxy-3-(tetradecyloxy)phenoxy]phosphinyl]oxy]phenyl]methyl]-pyridinium,hydroxide, inner salt

To a solution of 2.3 g of3-(bromomethyl)phenyl-2-methoxy-3-(tetradecyloxy)phenyl phosphate in 15ml of dry toluene was added 2.62 g of pyridine followed by stirring, inan inert atmosphere, at 60°-65° C. for 18 hours. The solvent was removedin vacuo and the residue stirred with 6.0 g of Amberlite® IR-4B resin in50 ml of methyl alcohol for 10 minutes. The mixture was filtered and thesolvent removed in vacuo. The residue was columned on silica gel withmethyl alcohol-chloroform and methyl alcohol-chloroform-water.Triturated with ether and refrigerated giving 1.4 g of the desiredcompound as a white amorphous powder.

EXAMPLE 271-[[3-[[Hydroxy[2-methoxy-3-(tetradecyloxy)phenoxy]phosphinyl]oxy]phenyl]methyl]-quinolinium,hydroxide, inner salt

To a solution of 2.0 g of 3-(bromomethyl)phenyl2-methoxy-3-(tetradecyloxy)phenyl phosphate in 15 ml of dry toluene wasadded 2.21 g of quinoline followed by stirring, in an inert atmosphere,at 90° C. for 4 hours. The solvent was removed in vacuo and the residuestirred with 6.0 g of Amberlite® IR-4B resin in 50 ml of methyl alcoholfor 2 hours. The mixture was filtered and the solvent removed in vacuo.The residue was columned on silica gel with methyl alcohol-chloroformand methyl alcohol-chloroform-water. Triturated with ether andrefrigerated giving 1.6 g of the desired compound as a white amorphouspowder.

EXAMPLE 282-[[3-[[Hydroxy[2-methoxy-3-(tetradecyloxy)phenoxy]phosphinyl]oxy]phenyl]methyl]-isoquinolinium,hydroxide, inner salt

To a solution of 1.7 g of 3-(bromomethyl)phenyl2-methoxy-3-(tetradecyloxy)phenyl phosphate in 15 ml of dry toluene wasadded 1.87 g of isoquinoline followed by stirring, in an inertatmosphere, at 80° C. for 5 hours. The solvent was removed in vacuo andthe residue stirred with 3.0 g of Amberlite® IR-4B resin in 60 ml ofmethyl alcohol for 15 minutes. The mixture was filtered and the solventremoved in vacuo. The residue was columned on silica gel with methylalcohol-chloroform and methyl alcohol-chloroform-water. Triturated withether and refrigerated giving 1.25 g of the desired product as a whiteamorphous powder.

EXAMPLE 29 Methyl 2-hydroxy-6-(tetradecyloxy)benzoate

To a suspension of 6.2 g of hexanes washed sodium hydride in 75 ml ofN,N-dimethylformamide was added dropwise over 1.5 hours a solution of20.0 g of methyl 2,6-dihydroxybenzoate in 50 ml of N,N-dimethylformamideand 24 ml of tetrahydrofuran. The resulting mixture was cooled to 0° C.and 1.78 g of sodium iodide added followed by the dropwise addition of34.7 g of 1-bromotetradecane over 1 hour. The bath was removed and themixture stirred at ambient temperature for 17 hours. The mixture wasdiluted with 500 ml of iced dilute hydrochloric acid, and extracted withether. The ether layer was dried over magnesium sulfate and evaporatedto an oil which was purified by chromatography on silica gel with ethylacetate:hexanes giving an oil which was distilled in a Kugelrohrapparatus giving 3.0 g of the desired compound as a white solid, B.P.130°-180° C.

EXAMPLE 30 Methyl 2-[[[3-(bromomethyl)phenoxy]hydroxyphosphinyl]oxy]-6-(tetradecyloxy)benzoate

To a solution of 2.9 g of methyl 2-hydroxy-6-(tetradecyloxy)benzoate in35 ml of dry carbon tetrachloride cooled in an ice bath was added asolution of 2.9 g of 3-(bromomethyl)phenyl phosphodichlorodate in aninert atmosphere. A solution of 1.4 ml of triethylamine in 10 ml ofcarbon tetrachloride was rapidly added followed by cooling bath removaland stirring overnight. The mixture was filtered through diatomaceousearth and evaporated to a residue which was stirred for 1.5 hours with70 ml of tetrahydrofuran and 70 ml of 0.5M sodium acetate. Thetetrahydrofuran was removed under vacuum and the aqueous residue cooledand acidified with hydrochloric acid followed by ether extraction. Theorganic layer was washed with saturated sodium chloride, dried withmagnesium sulfate and evaporated to a syrup which was purified bychromatography on magnesium silicate with chloroform and 10% methylalcohol-chloroform giving 3.6 g of the desired compound as a glass.

EXAMPLE 313-[[3-[[Hydroxy[2-(methoxycarbonyl)-3-(tetradecyloxy)phenoxy]phosphinyl]oxy]phenyl]methyl]-thiazolium,hydroxide, inner salt

To a solution of 1.10 g of methyl2-[[[3-(bromomethyl)phenoxy]hydroxyphosphinyl]oxy]-6-(tetradecyloxy)benzoatein 15 ml of dry toluene was added 1.31 g of thiazole followed bystirring, in an inert atmosphere, at 65°-70° C. for 17 hours. Thesolvent was removed in vacuo and the residue stirred with 1.26 g ofAmberlite® IR-4B resin in 50 ml of methyl alcohol for 2 hours. Themixture was filtered and the solvent removed in vacuo. The residue wascolumned on silica gel with methyl alcohol-chloroform and methylalcohol-chloroform-water. Triturated with ether and refrigerated giving532 mg of the desired compound as a white amorphous glass.

EXAMPLE 323-[[3-[[Hydroxy[2-(methoxycarbonyl)-3-(tetradecyloxy)phenoxy]phosphinyl]oxy]phenyl]methyl]-5-methylthiazolium,hydroxide, inner salt

To a solution of 1.18 g of methyl2-[[[3-(bromomethyl)phenoxy]hydroxyphosphinyl]oxy]-6-(tetradecyloxy)benzoatein 15 ml of dry toluene was added 1.53 g of 5-methylthiazole followed bystirring, in an inert atmosphere, at 65°-70° C. for 17 hours. Thesolvent was removed in vacuo and the residue stirred with 1.2 g ofAmberlite® IR-4B resin in 50 ml of methyl alcohol for 2 hours. Themixture was filtered and the solvent removed in vacuo. The residue wascolumned on silica gel with methyl alcohol-chloroform and methylalcohol-chloroform-water. Triturated with ether and refrigerated giving0.783 g of the desired compound as a white amorphous glass.

EXAMPLE 331-[[3-[[Hydroxy[2-(methoxycarbonyl)-3-(tetradecyloxy)phenoxy]phosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

To a solution of 1.18 g of methyl2-[[[3-(bromomethyl)phenoxy]hydroxyphosphinyl]oxy]-6-(tetradecyloxy)benzoatein 15 ml of dry toluene was added 1.99 g of quinoline followed bystirring, in an inert atmosphere, at 65°-70° C. for 17 hours. Thesolvent was removed in vacuo and the residue stirred with 1.2 g ofAmberlite® IR-4B resin in 50 ml of methyl alcohol for 1.5 hours. Themixture was filtered and the solvent removed in vacuo. The residue wascolumned on silica gel with methyl alcohol-chloroform and methylalcohol-chloroform-water. Triturated with ether and refrigerated giving0.846 g of the desired compound as a white powdered glass.

EXAMPLE 34 3-(Tetradecyloxy)benzyl alcohol

A mixture of 66 g of 3-hydroxyphenethyl alcohol, 147.43 g of1-bromotetradecane, 27.65 g of sodium hydroxide and 2.15 g oftrioctylmethyl ammonium chloride in 400 ml of toluene was refluxed for42 hours. The mixture was washed with water and the organic layer driedwith magnesium sulfate. The solvent was removed in vacuo and the warmconcentrate poured into 1 liter of hexanes. The resulting solid waswashed with cold hexanes then dried giving 998.6 g of the desiredcompound as a white solid.

EXAMPLE 35 Methyl 3-(bromomethyl)phenyl[3-(tetradecyloxy) phenylphosphate

To a solution of 9.0 g of 3-(tetradecyloxy)benzyl alcohol in 60 ml ofdry carbon tetrachloride cooled in an ice bath was added a solution of10.24 g of 3-(bromomethyl)phenyl phosphodichlorodate in 10 ml of carbontetrachloride in an inert atmosphere. A solution of 4.7 ml oftriethylamine in 10 ml of carbon tetrachloride was rapidly addedfollowed by cooling bath removal and stirring for 4 hours. The mixturewas filtered through diatomaceous earth and evaporated to a residuewhich was stirred for 1 hour with 150 ml of tetrahydrofuran and 150 mlof 0.5M sodium acetate. The tetrahydrofuran was removed under vacuum andthe aqueous residue cooled and acidified with hydrochloric acid followedby other extraction. The organic layer was washed with saturated sodiumchloride, dried with magnesium sulfate and evaporated to a syrup whichwas purified by chromatography on magnesium silicate with chloroform and10% methyl alcohol-chloroform giving 12.5 g of the desired compound as aglass.

EXAMPLE 363-[[3-[[Hydroxy[[3-(tetradecyloxy)phenyl]methoxy]phosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

To a solution of 3.0 g of 3-[(tetradecyloxy)benzyl alcohol in 20 ml ofdry toluene was added 1.1 g of thiazole followed by stirring, in aninert atmosphere, at 60°-75° C. for 2 days. The solvent was removed invacuo and the residue stirred with 3.0 g of Amberlite® IR-4B resin in 40ml of methyl alcohol for 2 hours. The mixture was filtered and thesolvent removed in vacuo. The residue was columned on silica gel withmethyl alcohol-chloroform and methyl alcohol-chloroform-water.Triturated with ether and refrigerated giving 0.4 g of the desiredcompound as a white amorphous powder.

EXAMPLE 37 3-Methoxy-1-tetradecyl-benzene

A 4.87 g portion of magnesium was placed in a two-necked round bottomflask. The flask was flamed several times and 37.4 g of m-bromoanisoleand 200 ml of tetrahydrofuran were added. As soon as the reactionstopped it was refluxed for 1 hour and then added to a boiling solutionof 52.68 g of tetradecyl bromide in tetrahydrofuran. Then 10 ml oflithium cupric chloride was added and the mixture was refluxed for 1.25hours, stirred at room temperature for 16 hours, quenched with water,washed with ammonium chloride solution, brine, dried and the solventremoved. The resulting oily residue was distilled in a Kugelrohrapparatus giving 52.4 g of the desired compound as a clear oil, B.P.(120°/0.5 mm).

EXAMPLE 38 3-Tetradecylphenol

To a solution of 136.8 g of 3-methoxy-1-tetradecylbenzene in 600 ml ofmethylene chloride, cooled to -78° C., under inert gas, was addeddropwise a solution of 112.8 g of boron tribromide in 100 ml ofmethylene chloride. The mixture was kept at -78° C. for 1 hour thenallowed to warm slowly to room temperature followed by stirring for 16hours. The mixture was cooled to 0° C. and cold water added dropwise.The organic layer was separated and washed with aqueous sodiumbicarbonate, dried and the solvent evaporated. The residue was pouredonto crushed ice and 107 g of the desired product collected as a whitesolid, m.p. 38°-40° C.

EXAMPLE 39 3-(Bromomethyl)phenyl 3-(tetradecyl)phenyl phosphate

A mixture of 1.5 g of 3-tetradecylphenol, 1.88 g of3-(bromomethyl)phenyl phosphodichlorodate and 627 mg of triethylamine in15 ml of carbon tetrachloride was stirred at room temperature for 4hours and filtered. The solvent was removed in vacuo and the residuestirred with 60 ml of 0.5M sodium acetate and 60 ml of tetrahydrofuranfor 1.5 hours. The mixture was poured into dilute hydrochloric acid andextracted with ether. The ether layer was washed with water, dried withmagnesium sulfate and filtered through a column of magnesium silicategiving 1.5 g of the desired product as an oil.

EXAMPLE 403-[[3-[[Hydroxy(3-tetradecylphenoxy)phosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

A mixture of 1.5 g of 3-(bromomethyl)phenyl 3-(tetradecyl)phenylphosphate and 1.89 g of thiazole was heated in 10 ml of toluene under aninert atmosphere for 2 hours. The solvent was removed in vacuo and theresidue purified by chromatography on silica gel using methylalcohol-chloroform and methyl alcohol-chloroform-water. Triturated withether and refrigerated giving 0.7 g of white powder.

EXAMPLE 41 3-(Dodecyloxy)phenol

To a suspension of 24.67 g of hexanes washed sodium hydride in 215 ml ofN,N-dimethylformamide was added dropwise over 1.5 hours a solution of54.33 g of resorcinol in 145 ml of N,N-dimethylformamide and 72 ml oftetrahydrofuran. The resulting mixture was cooled to 0° C. and 7.4 g ofsodium iodide added followed by the dropwise addition of 122.98 g of1-bromododecane over 1 hour. The bath was removed and the mixturestirred at ambient temperature for 17 hours. The mixture was dilutedwith 500 ml of cold dilute hydrochloric acid and extracted with ether.The ether layer was dried over magnesium sulfate and evaporated to a lowvolume and filtered. The filtrate was concentrated to a reddish oil andpurified by chromatography on silica gel using ethyl acetate-hexanes togive 36 g of the desired compound as buff colored crystals, m.p. 42°-43°C.

EXAMPLE 42 3-(Bromomethyl)phenyl 3-(dodecyloxy)phenyl phosphate

To a solution of 727 mg of 3-(dodecyloxy)phenol in 8 ml of dry carbontetrachloride cooled in an ice bath was added a solution of 952 mg of3-(bromomethyl)phenyl phosphodichlorodate in 2 ml of carbontetrachloride in an inert atmosphere. A solution of 317 mg oftriethylamine in 2 ml of carbon tetrachloride was rapidly added followedby cooling bath removal and stirring overnight. Added 10 ml of tolueneand filtered the mixture through diatomaceous earth. Evaporated thefiltrate to a residue which was stirred for 1.5 hours with 20 ml oftetrahydrofuran and 20 ml of 0.5M sodium acetate. The tetrahydrofuranwas removed under vacuum and the aqueous residue cooled and acidifiedwith hydrochloric acid followed by ether extraction. The organic layerwas washed with saturated sodium chloride, dried with magnesium sulfateand evaporated to a syrup which was purified by chromatography onmagnesium silicate with chloroform and 10% methyl alcohol-chloroformgiving 1.05 g of the desired compound as a glass.

EXAMPLE 433-[[3-[[[3-(Dodecyloxy)phenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

To a solution of 1.0 g of 3-(bromomethyl)phenyl 3-(dodecyloxy)phenylphosphate in 15 ml of dry toluene was added 1.29 g of thiazole followedby stirring, in an inert atmosphere, at 68° C. for 18 hours. The solventwas removed in vacuo and the residue stirred with 1.0 g of Amberlite®IR-4B resin in 30 ml of methyl alcohol for 1.5 hours. The mixture wasfiltered and the solvent removed in vacuo. The residue was columned onsilica gel with methyl alcohol-chloroform and methylalcohol-chloroform-water. Triturated with ether and refrigerated giving760 mg of the desired compound as white amorphous powder.

EXAMPLE 44 3-(Dodecyloxy)-2-methoxyphenol

To a suspension of 3.8 g of hexanes washed sodium hydride in 25 ml ofN,N-dimethylformamide, cooled to 0° C. in an inert atmosphere was addeda solution of 10 g of 2-methoxy resorcinol in 50 ml ofN,N-dimethylformamide dropwise over 20 minutes. Added 1.07 g of sodiumiodide followed by the dropwise addition of a solution of 19.8 g of1-bromododecane in 25 ml of N,N-dimethylformamide over 20 minutes. Thebath was removed and the mixture stirred at ambient temperature for 18hours. Added chips of ice followed by iced dilute hydrochloric acid. Themixture was extracted with ether and the organic layer dried withmagnesium sulfate and the solvent evaporated to an oil which wasdistilled in a Kugelrohr apparatus giving 10 g of an oil, B.P.120°-180°/0.1 mm. The oil was purified by chromatography on silica gelusing ether-hexanes giving 7.7 g of the desired product as an oilfollowing solvent removal.

EXAMPLE 45 3-(Bromomethyl)phenyl 3-(dodecyloxy)-2-(methoxy) phenylphosphate

To a solution of 7.2 g of 3-(dodecyloxy)-2-methoxyphenol in 45 ml ofcarbon tetrachloride was added 9.22 g of 3-(bromomethyl)phenylphosphodichlorodate. The mixture was cooled to 0° C. under inert gas and3.07 g of triethylamine in 10 ml of carbon tetrachloride carefully addeddropwise. The cooling bath was removed and the mixture stirred atambient temperature for 18 hours. The mixture was filtered throughdiatomaceous earth and the filtrate taken to dryness. The residue wasstirred with 225 ml of tetrahydrofuran and 225 ml of 0.5M sodium acetateat room temperature for 2 hours. The tetrahydrofuran was removed invacuo and the aqueous residue cooled to 0° C. and acidified withhydrochloric acid followed by ether extraction. The organic layer wasdried with magnesium sulfate and the solvent removed to afford a thickoil, which was purified by chromatography on magnesium silicate withchloroform and methyl alcohol-chloroform giving 8.1 g of the desiredproduct as a glass.

EXAMPLE 46-[[3-[[[3-(Dodecyloxy)-2-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

To a solution of 2 g of 3-(bromomethyl)phenyl3-(dodecyloxy)-2-methoxyphenyl phosphate in 15 ml of dry toluene wasadded 3.7 g of quinoline followed by stirring, in an inert atmosphere,at 65°-70° C. for 18 hours. The solvent was removed in vacuo and theresidue stirred with 3.0 g of Amberlite® IR-4B resin in 50 ml of methylalcohol for 1 hour. The mixture was filtered and the solvent removed invacuo. The residue was columned on silica gel with methylalcohol-chloroform and methyl alcohol-chloroform-water. Triturated withether and refrigerated giving 1.36 g of the desired compound as a whiteamorphous powder.

EXAMPLE 473-[[3-[[[3-(Dodecyloxy)-2-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

To a solution of 2 g of 3-(bromomethyl)phenyl3-(dodecyloxy)-2-(methoxy)phenyl phosphate in 15 ml of dry toluene wasadded 2.44 g of thiazole followed by stirring, in an inert atmosphere,at 65°-70° C. for 24 hours. The solvent was removed in vacuo and theresidue stirred with 3.0 g of Amberlite® IR-4B resin in 50 ml of methylalcohol for 2 hours. The mixture was filtered and the solvent removed invacuo. The residue was columned on silica gel with methylalcohol-chloroform and methyl alcohol-chloroform-water. Triturated withether and refrigerated giving 1.13 g of the desired compound as ayellow-orange glass.

EXAMPLE 48 4,6-Bis(1,1-dimethylethyl)-3-(dodecyloxy)phenol

To a suspension of 21.04 g of hexanes washed sodium hydride in 200 ml ofN,N-dimethylformamide under argon was added 5.06 g of sodium iodidefollowed by the dropwise addition of 75 g of 4,6-di-t-butyl resorcinoldissolved in 200 ml of N,N-dimethylformamide and 150 ml oftetrahydrofuran over 1 hour. Over a 30 minute period, 84.1 g of1-bromododecane was added dropwise followed by stirring for 18 hours.The mixture was poured into water and extracted with ether. The organiclayer was washed with water and dried with magnesium sulfate. Thesolvent was evaporated and the oily concentrate distilled to give 38 gof the desired compound as an orange oil, B.P. 180°-205° C./0.5 mm.

EXAMPLE 49 2,4-Bis(1,1-dimethylethyl)-5-(dodecyloxy)phenyl3-(bromomethyl)phenyl phosphate

To a solution of 2.0 g of4,6-bis(1,1-dimethylethyl)-3-(dodecyloxy)phenol in 30 ml of dry carbontetrachloride cooled in an ice bath was added a solution of 1.9 g of3-(bromomethyl)phenyl phosphodichlorodate in an inert atmosphere. Asolution of 0.9 ml of triethylamine in 5 ml of carbon tetrachloride wasrapidly added followed by cooling bath removal and stirring overnight.The mixture was filtered through diatomaceous earth and evaporated to aresidue which was stirred for 1.5 hours with 65 ml of tetrahydrofuranand 65 ml of 0.5M sodium acetate. The tetrahydrofuran was removed undervacuum and the aqueous residue cooled and acidified with hydrochloricacid followed by ether extraction. The organic layer was washed withsaturated sodium chloride, dried with magnesium sulfate and evaporatedto a syrup which was purified by chromatography on magnesium silicatewith chloroform and 10% methyl alcohol-chloroform giving 1.4 g of thedesired compound as a glass.

EXAMPLE 50 3-[[3-[[[2,4-Bis(1,1-dimethylethyl)-5-(dodecyloxy)phenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

To a solution of 1.35 g of2,4-bis(1,1-dimethylethyl)-5-(dodecyloxy)phenyl 3-(bromomethyl)phenylphosphate in 15 ml of dry toluene was added 1.44 g of thiazole followedby stirring, in an inert atmosphere, at 65°-70° C. for 17 hours. Thesolvent was removed in vacuo and the residue stirred with 1.5 g ofAmberlite® IR-4B resin in 50 ml of methyl alcohol for 2 hours. Themixture was filtered and the solvent removed in vacuo. The residue wascolumned on silica gel with methyl alcohol-chloroform and methylalcohol-chloroform-water. Triturated with ether and refrigerated giving0.643 g of the desired compound as beige amorphous powder.

EXAMPLE 51 2,5-Bis(1,1-dimethylethyl)-4-(dodecyloxy)phenol

To a suspension of 42.08 g of hexanes washed sodium hydride, under inertgas, in 400 ml of N,N-dimethylformamide was added 10.12 g of sodiumiodide. White stirring, a solution of 150 g of2,5-di-tert-butylhydroquinone in 400 ml of N,N-dimethylformamide and 300ml of tetrahydrofuran was added dropwise over 1.5 hours. Over anadditional 30 minutes, 168.16 g of 1-bromododecane was added dropwise.Stirring was continued at ambient temperature for 24 hours. The mixturewas diluted with crushed ice and cold dilute hydrochloric acid followedby ether extraction. The organic layer was dried with magnesium sulfateand the solvent removed in vacuo to afford a syrup which was distilledin a Kugelrohr apparatus. The fraction boiling 160°-205° C. wascollected and purified by chromatography on silica gel withether-hexanes giving 23.6 g of the desired compound as an orange oil.

EXAMPLE 52 2,5-Bis(1,1-dimethylethyl)-4-(dodecyloxy)phenyl3-(bromomethyl)phenyl phosphate

To a solution of 2.0 g of2,5-bis(1,1-dimethylethyl)-4-(dodecyloxy)phenol in 30 ml of dry carbontetrachloride cooled in an ice bath was added a solution of 1.9 g of3-(bromomethyl)phenyl phosphodichlorodate in an inert atmosphere. Asolution of 0.9 ml of triethylamine in 10 ml of carbon tetrachloride wasrapidly added followed by cooling bath removal and stirring for 4 hours.The mixture was filtered through diatomaceous earth and evaporated to aresidue which was stirred for two hours with 65 ml of tetrahydrofuranand 65 ml of 0.5M sodium acetate. The tetrahydrofuran was removed undervacuum and the aqueous residue cooled and acidified with hydrochloricacid followed by ether extraction. The organic layer was washed withsaturated sodium chloride, dried with magnesium sulfate and evaporatedto a syrup which was purified by chromatography on magnesium silicatewith chloroform and 10% methyl alcohol-chloroform giving 2.0 g of thedesired product as a glass.

EXAMPLE 533-[[3-[[[2,5-Bis(1,1-dimethylethyl)-4-(dodecyloxy)phenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

To a solution of 1.95 g of2,5-bis(1,1-dimethylethyl)-4-(dodecyloxy)phenyl 3-(bromomethyl)phenylphosphate in 15 ml of dry toluene was added 2.0 g of thiazole followedby stirring, in an inert atmosphere, at 65°-70° C. for 18 hours. Thesolvent was removed in vacuo and the residue stirred with 2.0 g ofAmberlite® IR-4B resin in 60 ml of methyl alcohol for 2 hours. Themixture was filtered and the solvent removed in vacuo. The residue wascolumned on silica gel with methyl alcohol-chloroform and methylalcohol-chloroform-water. Triturated with ether and refrigerated giving0.83 g of the desired compound as an amorphous solid.

EXAMPLE 543-[[3-[[[2,5-Bis(1,1-dimethylethyl)-4-(dodecyloxy)phenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-5-methyl-thiazolium,hydroxide, inner salt

To a solution of 1.4 g of2,5-bis(1,1-dimethylethyl)-4-(dodecyloxy)phenyl 3-(bromomethyl)phenylphosphate in 15 ml of dry toluene was added 1.8 g of 5-methylthiazolefollowed by stirring, in an inert atmosphere, at 70° C. for 24 hours.The solvent was removed in vacuo and the residue stirred with 1.5 g ofAmberlite® IR-4B resin in 40 ml of methyl alcohol for 1.5 hours. Themixture was filtered and the solvent removed in vacuo. The residue wascolumned on silica gel with methyl alcohol-chloroform and methylalcohol-chloroform-water. Triturated with ether and refrigerated giving0.56 g of the desired compound as a white amorphous glass.

EXAMPLE 551-[[3-[[[2,5-Bis(1,1-dimethylethyl)-4-(dodecyloxy)phenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

To a solution of 1.4 g of2,5-bis(1,1-dimethylethyl)-4-(dodecyloxy)phenyl 3-(bromomethyl)phenylphosphate in 15 ml of dry toluene was added 2.3 g of quinoline followedby stirring, in an inert atmosphere, at 70° C. for 24 hours. The solventwas removed in vacuo and the residue stirred with 1.5 g of Amberlite®IR-4B resin in 40 ml of methyl alcohol for 1.5 hours. The mixture wasfiltered and the solvent removed in vacuo. The residue was columned onsilica gel with methyl alcohol-chloroform and methylalcohol-chloroform-water. Triturated with ether and refrigerated giving1.04 g of the desired product as a hard glass.

EXAMPLE 56 7-(Dodecyloxy)-2-naphthalenol

To a suspension of 19.47 g of hexane washed sodium hydride in 200 ml ofN,N-dimethylformamide was added dropwise over 1 hour a solution of 50.0g of 2,7-dihydroxynaphthalene in 100 ml of N,N-dimethylformamide and 200ml of tetrahydrofuran. The resulting mixture was cooled to 0° C. and7.25 g of sodium iodide added followed by the dropwise addition of 92.47g of 1-iodododecane over 1 hour. The bath was removed and the mixtureheated at 60° C. then stirred at ambient temperature for 18 hours. Themixture was diluted with 500 ml of dilute hydrochloric acid andextracted with ether. The ether layer was dried over magnesium sulfateand evaporated to an oil which was distilled in a Kugelrohr apparatusand the fraction boiling from 170°-250° C./3 mm collected as a solidfollowed by crystallization from methyl alcohol then hexane giving 10.1g of the desired compound as a white solid.

EXAMPLE 57 3-(Bromomethyl)phenyl 7-(dodecyloxy)-2-naphthalenyl phosphate

To a solution of 0.22 g of 7-(dodecyloxy)-2-naphthalenol in 5 ml of drycarbon tetrachloride was added 0.244 g of 3-(bromomethyl)phenylphosphodichlorodate in an inert atmosphere. A solution of 0.12 ml oftriethylamine in 1 ml of carbon tetrachloride was rapidly added followedby stirring at ambient temperature for 4 hours and refrigeration for twodays. The mixture was filtered through diatomaceous earth and evaporatedto a residue which was stirred for two hours with 20 ml oftetrahydrofuran and 20 ml of 0.5M sodium acetate. The tetrahydrofuranwas removed under vacuum and the aqueous residue cooled and acidifiedwith hydrochloric acid followed by ether extraction. The organic layerwas washed with saturated sodium chloride, dried with magnesium sulfateand evaporated giving the desired compound as a syrup.

EXAMPLE 583-[[3-[[[[7-(dodecyloxy)-2-naphthalenyl]oxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

To a solution of 0.22 g of 7-(dodecyloxy)-2-naphthalenol in 5 ml of drytoluene was added 0.5 g of thiazole followed by stirring, in an inertatmosphere, at 65°-70° C. for 18 hours and allowed to stand at ambienttemperature for 2 days. The solvent was removed in vacuo and the residuestirred with 500 mg of Amberlite® IR-4B resin in 20 ml of methyl alcoholfor 1.5 hours. The mixture was filtered and the solvent was removed invacuo. The residue was columned on silica gel with methylalcohol-chloroform and methyl alcohol-chloroform-water. Triturated withether and refrigerated giving 234 mg of the desired compound as a whiteamorphous powder.

EXAMPLE 593-[[3-[[(3-Chlorophenoxy)hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

A mixture of 3 g of 3-chlorophenol and 7.09 g of 3-(bromomethyl)phenylphosphodichlorodate in 50 ml of carbon tetrachloride was stirred while2.83 g of triethylamine was added. Stirring was continued for 5 hoursthen diluted with ether and filtered. The solvent was removed in vacuoand the residue stirred for 2 hours with 250 ml of 0.5M sodium acetateand 250 ml of tetrahydrofuran. The tetrahydrofuran was removed in vacuoand the aqueous residue acidified with hydrochloric acid followed byether extraction. The organic layer was dried with magnesium sulfate andthe solvent evaporated. The residue was heated with 9.93 g of thiazolein 50 ml of toluene in an inert atmosphere at 85° C. for 5 hours, cooledto ambient temperature and the toluene decanted from the precipitatedoil. The oil was dissolved in 150 ml of warm methyl alcohol and stirredwith 20 g of Amberlite® IR-45 and 4 ml of water for 20 minutes. Themixture was filtered and the solvent evaporated. The residue waschromatographed on silica gel using chloroform-methanol-water.Evaporation of the fractions and triturated with ether followed bycentrifuging gave 3.7 g of the desired product as a white powder.

EXAMPLE 60 3-(Bromomethyl)phenyl 4-chlorophenyl phosphate

To a solution of 2 g of 4-chlorophenol in 35 ml of carbon tetrachloridewas added 5.2 g of 3-(bromomethyl)phenyl phosphodichlorodate. Themixture was cooled to 0° C. under inert gas and 2.6 g of triethylaminecarefully added. The cooling bath was removed and the mixture stirred atambient temperature for 5 hours followed by standing in a refrigeratorfor 18 hours. The mixture was filtered through diatomaceous earth andthe filtrate taken to dryness. The residue was stirred with 165 ml oftetrahydrofuran and 165 ml of 0.5M sodium acetate at room temperaturefor 2 hours. The tetrahydrofuran was removed in vacuo and the aqueousresidue cooled to 0° C. and acidified with hydrochloric acid followed byether extraction. The organic layer was dried with magnesium sulfate andthe solvent removed to afford a thick oil which was purified bychromatography on magnesium silicate with chloroform and methylalcohol-chloroform giving 3.9 g of the desired product as a glass.

EXAMPLE 611-[[3-[[(4-Chlorophenoxy)hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

To a solution of 1.3 g of 3-(bromoethyl)phenyl 4-chlorophenyl phosphatein 15 ml of dry toluene was added 3.56 g of quinoline followed bystirring, in an inert atmosphere, at 70° C. for 72 hours. The solventwas removed in vacuo and the residue stirred with 2.0 g of Amberlite®IR-4B resin in 50 ml of methyl alcohol for 2 hours. The mixture wasfiltered and the solvent removed in vacuo. The residue was columned onsilica gel with methyl alcohol-chloroform and methylalcohol-chloroform-water. Triturated with ether and refrigerated giving7.1 mg of the desired compound as a white amorphous solid.

EXAMPLE 623-[[3-[[(4-Chlorophenoxy)hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

To a solution of 1.3 g of 4-chlorophenyl phosphate in 15 ml of drytoluene was added 2.34 g of thiazole followed by stirring, in an inertatmosphere, at 70° C. for 17 hours. The solvent was removed in vacuo andthe residue stirred with 2.0 g of Amberlite® IR-4B resin in 50 ml ofmethyl alcohol for 1.5 hours. The mixture was filtered and the solventremoved in vacuo. The residue was columned on silica gel with methylalcohol-chloroform and methyl alcohol-chloroform-water. Triturated withether and refrigerated giving 0.53 g of the desired compound as a whiteamorphous solid.

EXAMPLE 63 3-(Bromomethyl)phenyl-2-chlorophenyl phosphate

To a solution of 2 g of 2-chlorophenol in 35 ml of carbon tetrachloridewas added 5.2 g of 3-(bromomethyl)phenyl phosphodichlorodate. Themixture was cooled to 0° C. under inert gas and 2.6 ml of triethylaminecarefully added. The cooling bath was removed and the mixture stirred atambient temperature for 5 hours followed by standing in a refrigeratorfor 18 hours. The mixture was filtered through diatomaceous earth andthe filtrate taken to dryness. The residue was stirred with 165 ml oftetrahydrofuran and 165 ml of 0.5M sodium acetate at room temperaturefor 2 hours. The tetrahydrofuran was removed in vacuo and the aqueousresidue cooled to 0° C. and acidified with hydrochloric acid followed byether extraction. The organic layer was dried with magnesium sulfate andthe solvent removed to afford a thick oil, which was purified bychromatography on magnesium silicate with chloroform and methylalcohol-chloroform giving 3.8 g of the desired product as an oil.

EXAMPLE 64 3-[[3-[[2-Chlorophenoxy)hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

To a solution of 1.3 g of 3-(bromomethyl)phenyl-2-chlorophenyl phosphatein 15 ml of dry toluene was added 2.34 g of thiazole followed bystirring, in an inert atmosphere, at 70° C. for 17 hours. The solventwas removed in vacuo and the residue stirred with 2.0 g of Amberlite®IR-4B resin in 50 ml of methyl alcohol for 1.5 hours. The mixture wasfiltered and the solvent removed in vacuo. The residue was columned onsilica gel with methyl alcohol-chloroform and methylalcohol-chloroform-water. Triturated with ether and refrigerated giving377 mg of the desired compound as a white amorphous solid.

EXAMPLE 651-[[3-[[(2-Chlorophenoxy)hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

To a solution of 1.3 g of 3-(bromomethyl)phenyl-2-chlorophenyl phosphatein 15 ml of dry toluene was added 3.56 g of quinoline followed bystirring, in an inert atmosphere, at 70° C. for 72 hours. The solventwas removed in vacuo and the residue stirred with 2.0 g of Amberlite®IR-4B resin in 50 ml of methyl alcohol for 2 hours. The mixture wasfiltered and the solvent removed in vacuo. The residue was columned onsilica gel with methyl alcohol-chloroform and methylalcohol-chloroform-water. Triturated with ether and refrigerated giving743 mg of the desired compound as an amorphous solid.

EXAMPLE 663-[[3-[[([1,1'-Biphenyl]-3-yloxy)hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

A mixture of 3.0 g of 3-phenylphenol and 5.36 g of 3-(bromomethyl)phenylphosphodichlorodate in 50 ml of carbon tetrachloride was stirred while2.14 g of triethylamine was added. Stirring was continued for 4 hours,diluted with ether and filtered. The ether was removed and the residuestirred for 2 hours with 200 ml of 0.5M sodium acetate and 200 ml oftetrahydrofuran. The tetrahydrofuran was removed in vacuo and theaqueous residue acidified with hydrochloric acid followed by etherextraction. The organic layer was dried with magnesium sulfate and thesolvent evaporated. The residue was heated with 7.5 g of triazole in 45ml of toluene in an inert atmosphere at 85° C. for 4 hours followed bycooling. The toluene was decanted and the residue slurried with 150 mlof hot methyl alcohol followed by the addition of 20 g of Amberlite®IR-45 resin. After stirring for 30 minutes, the mixture was filtered andthe solvent evaporated. The residue was chromatographed on silica gelusing chloroform-methanol-water giving 2.2 g of the desired product as awhite powder following stirring with ether, filtering and drying.

EXAMPLE 673-[[3-[[Hydroxy[4-(phenylmethoxy)phenoxy]phosphinyl]oxy]phenyl]methyl]-5-methyl-thiazolium,hydroxide, inner salt

A mixture of 3 g of 4-(benzyloxy)phenol and 4.6 g of3-(bromomethyl)phenyl phosphodichlorodate in 50 ml of carbontetrachloride was stirred while 1.8 g of triethylamine was added.Stirring was continued for 5 hours, diluted with ether and filtered. Theether was removed and the residue stirred for 3 hours with 200 ml of0.5M sodium acetate and 200 ml of tetrahydrofuran. The tetrahydrofuranwas removed in vacuo and the aqueous residue acidified with hydrochloricacid followed by ether extraction. The organic layer was dried withmagnesium sulfate and the solvent evaporated. The residue was heatedwith 6.38 g of 5-methyl thiazole in 45 ml of toluene under an inertatmosphere at 85° C. for 5 hours. The mixture was cooled and the toluenedecanted. The residue was dissolved in 200 ml of methyl alcohol andstirred with 20 g of Amberlite® IR-45 resin. After stirring for 30minutes, the mixture was filtered and the solvent evaporated. Theresidue was chromatographed on silica gel using chloroform-methylalcohol and chloroform-methyl alcohol-water giving 1.6 g of the desiredproduct as a white powder following stirring with ether, filtering anddrying.

EXAMPLE 68 Octadecyl 3-hydroxy-2-methylphenyl carbamate

To a suspension of 7.7 g of hexane washed sodium hydride in 100 ml oftetrahydrofuran was added dropwise over 10 minutes a solution of 20 g of2-methylresorcinol in 100 ml of tetrahydrofuran. After stirring for 1hour, a solution of 56 ml of octadecylisocyanate in 50 ml oftetrahydrofuran was rapidly added dropwise followed by stirring for 15hours at room temperature. The mixture was poured into saturatedammonium chloride and extracted with ether. The organic layer was driedwith sodium sulfate and evaporated to a waxy solid which was purified bychromatography on silica gel using ethyl acetate-hexanes, and giving17.5 g of the desired product as a waxy solid.

EXAMPLE 693-[[3-[[Hydroxy[2-methyl-3-[[(octadecylamino)carbonyl]oxy]phenoxy]phosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

To a solution of 5 g of octadecyl 3-hydroxy-2-methylphenyl carbamate in100 ml of carbon tetrachloride was added 2.5 ml of triethylaminefollowed by a solution of 4.5 g of 3-(bromomethyl)phenylphosphodichlorodate in 20 ml of carbon tetrachloride. After stirring atambient temperature for 15 hours, the mixture was filtered throughdiatomaceous earth and evaporated. The residue was stirred with 30 ml oftetrahydrofuran and 15 ml of 0.5N sodium acetate for 1 hour thenacidified with 5% hydrochloric acid and extracted with ethyl acetate.The organic layer was dried with sodium sulfate and evaporated. Theresidue was dissolved in 20 ml of toluene and 1.4 ml of thiazole addedfollowed by heating at 90° C. for 5 hours. The volatiles were removed invacuo and 50 ml of methyl alcohol added to the residue followed bystirring with 2 g of Amberlite® A-21 resin for 2 hours. The mixture wasfiltered and the solvent removed in vacuo. The residue was purified bychromatography on silica gel using chloroform-methyl alcohol-water. Thedesired compound was obtained as a waxy solid.

EXAMPLE 703-[[3-[[Hydroxy[2-methyl-3-[[(octadecylamino)carbonyl]oxy]phenoxy]phosphinyl]oxy]phenyl]methyl]-5-methylthiazolium,hydroxide, inner salt

To a solution of 1.26 g of octadecyl 3-hydroxy-2-methylphenyl carbamatein 100 ml of carbon tetrachloride was added 2.5 ml of triethylaminefollowed by a solution of 1.13 g of 3-(bromomethyl)phenylphosphodichlorodate in 20 ml of carbon tetrachloride. After stirring atambient temperature for 15 hours, the mixture was filtered throughdiatomaceous earth and evaporated. The residue was stirred with 30 ml oftetrahydrofuran and 15 ml of 0.5N sodium acetate for 1 hour thenacidified with 5% hydrochloric acid and extracted with ethyl acetate.The organic layer was dried with sodium sulfate and evaporated. Theresidue was dissolved in 20 ml of toluene and 1.4 ml of 5-methylthiazolefollowed by heating at 90° C. for 5 hours. The volatiles were removed invacuo and 50 ml of methyl alcohol added to the residue followed bystirring with 2 g of Amberlite® A-21 resin for 2 hours. The mixture wasfiltered and the solvent removed in vacuo. The residue was purified bychromatography on silica gel using chloroform-methyl alcohol-water. Thedesired product weighing 555 mg was obtained as a waxy solid.

EXAMPLE 71 2,5-Dichloro-4-(tetradecyloxy)phenol

To a suspension of 14.86 g of hexanes washed sodium hydride in 100 ml ofN,N-dimethylformamide containing 4.19 g of sodium iodide and cooled to0° C. was added a solution of 50 g of 2,5-dichloro-4-hydroxyphenol in200 ml of N,N-dimethylformamide over 1 hour. A solution of1-bromotetradecane in 100 ml of N,N-dimethylformamide was added over 10minutes. The bath was removed and the mixture stirred at ambienttemperature for 18 hours. The mixture was poured into dilutehydrochloric acid and extracted with ether then filtered. The etherlayer was separated, washed with brine and dried over magnesium sulfate.The ether was removed by evaporation and the concentrate distilled usinga Kugelrohr apparatus. The fraction boiling at 130°-180° C./0.1 mm wascollected and chromatographed on silica gel with hexanes-ether giving15.2 g of the desired compound as a white solid following hexanescrystallization.

EXAMPLE 72 3-(Bromomethyl)phenyl 2,5-dichloro-4-(tetradecyloxy)phenylphosphate

To a solution of 8.0 g of 2,5-dichloro-4-(tetradecyloxy)phenol in 50 mlof dry carbon tetrachloride was added a solution of 4.86 g of3-(bromomethyl)phenyl phosphodichlorodate in 10 ml of carbontetrachloride in an inert atmosphere. A solution of 1.86 g oftriethylamine in 10 ml of carbon tetrachloride was rapidly addedfollowed by and stirring for 4 hours. The mixture was filtered throughdiatomaceous earth and evaporated to a residue which was stirred for 3hours with 200 ml of tetrahydrofuran and 200 ml of 0.5M sodium acetate.The tetrahydrofuran was removed under vacuum and the aqueous layerextracted with ether. The organic layer was washed with saturated sodiumchloride, dried with magnesium sulfate and evaporated to give 9.0 g ofthe desired compound as an off white solid.

EXAMPLE 733-[[3-[[[2,5-Dichloro-4-(tetradecyloxy)phenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-5-methyl-thiazolium,hydroxide, inner salt

To a solution of 4.5 g of3-(bromomethyl)phenyl)-2,5-dichloro-4-(tetradecyloxy)phenyl phosphate in40 ml of dry toluene was added 3.58 g of 5-methyl thiazole followed bystirring, in an inert atmosphere, at 85° C. for 5 hours. The solvent wasremoved in vacuo and the residue stirred with 20 g of Amberlite® IR-4Bresin in 200 ml of methyl alcohol for 10 minutes. The mixture wasfiltered and the solvent removed in vacuo. The residue was columned onsilica gel with methyl alcohol-chloroform and methylalcohol-chloroform-water. Triturated with ether and refrigerated giving2.2 g of the desired compound as a white amorphous powder.

EXAMPLE 743-[[2-[[[2,5-Bis(1,1-dimethylethyl)-4-(dodecyloxy)phenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-2-methyl-thiazolium,hydroxide, inner salt

A suspension of 5 g of 2,5-bis(1,1-dimethylethyl)-4-dodecyloxyphenol,2.59 g of 2-chloro-4H-1,3,2-benzodioxaphosphorin, 2-oxide and 1.55 g oftriethylamine in 60 ml of carbon tetrachloride was stirred at roomtemperature for 5 hours followed by storing in a freezer for 2 days. Themixture was diluted with ether and filtered. The solvent was removedfrom the filtrate and the residue dissolved in 75 ml of acetonitrilecontaining 6.35 g of 5-methylthiazole and 191.8 mg of sodium iodide. Themixture was heated at 85° C. for 19 hours. The solvent was removed invacuo and the residue stirred with 200 ml of methyl alcohol and 20 g ofAmberlite® IR-45 resin for 1.5 hours. The mixture was filtered and thesolvent removed in vacuo. The residue was columned on silica gel withchloroform-methyl alcohol and chloroform-methyl alcohol-water. Dissolvedin ether and cooled giving 1.8 g of the desired compound as a whiteamorphous powder.

EXAMPLE 75 Octadecyl 2,5-bis (1,1-dimethylethyl)-4-hydroxyphenylcarbamate

To a suspension of 2.16 g of hexanes washed sodium hydride in 50 ml ofdry tetrahydrofuran was added a solution of 10 g ofdi-t-butylhydroquinone in 100 ml of tetrahydrofuran dropwise over 20minutes. After stirring for 1 hour, a solution of 13.3 g ofoctadecylisocyanate in 50 ml of tetrahydrofuran was added dropwise over20 minutes followed by stirring for 24 hours. The mixture was pouredinto saturated ammonium chloride and extracted with ether several times.The combined extracts were dried with magnesium sulfate and evaporatedto a syrup which was columned on silica gel with hexanes and ethylacetate-hexanes to give 2.93 g of the desired compound as a heavy yellowoil.

EXAMPLE 763-[[3-[[[2,5-Bis(1,1-dimethylethyl)-4-[[(octadecylamino)carbonyl]oxy]phenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

To a solution of 2.0 g of octadecyl2,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl carbamate in 10 ml of carbontetrachloride was added 0.84 ml of triethylamine followed by the slowaddition of 1.76 g of 3-(bromomethyl)phenyl phosphodichlorodatedissolved in 5 ml of carbon tetrachloride. The reaction was stirred atroom temperature for 1 hour. An additional 1 g of 3-(bromomethyl)phenylphosphodichlorodate was added followed by 1 ml of triethylamine andcontinued stirring for 48 hours. The mixture was refluxed for 1.5 hours.The solvent was evaporated and the residue stirred for 45 minutes with25 ml of tetrahydrofuran and 25 ml of 0.5N sodium acetate. The mixturewas acidified and extracted with ethyl acetate. The organic layer wasdried with sodium acetate and evaporated. The residue was dissolved in15 ml of toluene and 0.35 ml of thiazole added followed by heating at90° C. for 15 hours. The solvent was removed in vacuo and the residuestirred with 30 ml of methyl alcohol and 2 g of Amberlite® A-21 resinfor 1 hour. The mixture was filtered and the solvent removed in vacuo.The residue was columned on silica gel with chloroform-methylalcohol-water giving 800 mg of the desired compound as a white solid.

According to the methods described in detail hereinabove in Examples1-76, the compounds of this invention listed hereinbelow in Table II canbe prepared using the appropriate, hydroxy compound, phosphorousreagent, and nitrogen containing heterocycle. The hydroxy compoundsneeded to prepare these compounds are either articles of commerce or canbe obtained using the procedures described hereinabove in Flowsheets Eand F, in U.S. Pat. Nos. 4,697,031; 4,699,990 and 4,640,913, and in ourcopending patent application Ser. No. 177,299.

The phosphorous reagents are prepared as described hereinabove inFlowsheet C and D and in the patents and copending applicationsdescribed hereinabove. These methods are applicable to the preparationof the compounds of this invention by one skilled in the art.

TABLE II

3-[3-[[[3-(Hexadecyloxy)phenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-5-methylthiazolium,hydroxide, inner salt

3-[3-[[[3-(Hexadecyloxy)-2-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[3-[[[3-(Hexadecyloxy)-2-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[3-[[[3-(Hexadecyloxy)-2-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[3-[[[3-(Hexadecyloxy)-2-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-5-methylthiazolium,hydroxide, inner salt

3-[3-[[[3-(Hexadecyloxy)-2-nitrophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[3-[[[3-(Hexadecyloxy)-2-nitrophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-5-methylthiazolium,hydroxide, inner salt

3-[3-[[[3-(Hexadecyloxy)-2-carbomethoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[3-[[[3-(Hexadecyloxy)-2-carbomethoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-5-methylthiazolium,hydroxide, inner salt

3-[3-[[[3-(Hexadecyloxy)-5-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[3-[[[3-(Hexadecyloxy)-5-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-5-methylthiazolium,hydroxide, inner salt

3-[3-[[[3-(Hexadecyloxy)-5-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[3-[[[3-(Hexadecyloxy)-5-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-5-methylthiazolium,hydroxide, inner salt

3-[3-[[[3-(Tetradecyloxy)phenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[3-[[[3-(Tetradecyloxy)phenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-5-methylthiazolium,hydroxide, inner salt

3-[3-[[[3-(Tetradecyloxy)phenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[3-[[[3-(Tetradecyloxy)-2-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[3-[[[3-(Tetradecyloxy)-2-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-5-methylthiazolium,hydroxide, inner salt

3-[3-[[[3-(Tetradecyloxy)-2-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[3-[[[3-(Tetradecyloxy)-2-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[3-[[[3-(Tetradecyloxy)-2-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-5-methylthiazolium,hydroxide, inner salt

3-[3-[[[3-(Tetradecyloxy)-2-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[3-[[[3-(Tetradecyloxy)-2-nitrophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[3-[[[3-(Tetradecyloxy)-2-nitrophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-5-methylthiazolium,hydroxide, inner salt

3-[3-[[[3-(Tetradecyloxy)-2-nitrophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[3-[[[3-(Tetradecyloxy)-2-carbomethoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[3-[[[3-(Tetradecyloxy)-2-carbomethoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-5-methylthiazolium,hydroxide, inner salt

3-[3-[[[3-(Tetradecyloxy)-2-carbomethoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[3-[[[3-(Tetradecyloxy)-5-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[3-[[[3-(Tetradecyloxy)-5-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-5-methylthiazolium,hydroxide, inner salt

3-[3-[[[3-(Tetradecyloxy)-5-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[3-[[[3-(Tetradecyloxy)-5-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[3-[[[3-(Tetradecyloxy)-5-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-5-methylthiazolium,hydroxide, inner salt

3-[3-[[[3-(Tetradecyloxy)-5-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[3-[[[3-(Dodecyloxy)phenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[3-[[[3-(Dodecyloxy)phenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[3-[[[3-(Dodecyloxy)-2-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[3-[[[3-(Dodecyloxy)-2-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[3-[[[3-(Dodecyloxy)-2-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[3-[[[3-(Dodecyloxy)-2-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[3-[[[3-(Dodecyloxy)-2-nitrophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[3-[[[3-(Dodecyloxy)-2-nitrophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[3-[[[3-(Dodecyloxy)-2-carbomethoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[3-[[[3-(Dodecyloxy)-2-carbomethoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[3-[[[3-(Dodecyloxy)-5-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[3-[[[3-(Dodecyloxy)-5-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[3-[[[3-(Dodecyloxy)-5-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[3-[[[3-(Dodecyloxy)-5-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[3-[[[2-(Hexadecyloxy)phenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[3-[[[2-(Hexadecyloxy)phenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-5-methylthiazolium,hydroxide, inner salt

3-[3-[[[2-(Hexadecyloxy)-5-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[3-[[[2-(Hexadecyloxy)-5-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-5-methylthiazolium,hydroxide, inner salt

3-[3-[[[2-(Hexadecyloxy)-5-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[3-[[[2-(Hexadecyloxy)-5-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-5-methylthiazolium,hydroxide, inner salt

3-[3-[[[2-(Hexadecyloxy)-3-chlorophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[3-[[[2-(Hexadecyloxy)-3-chlorophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-5-methylthiazolium,hydroxide, inner salt

3-[3-[[[2-(Tetradecyloxy)phenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[3-[[[2-(Tetradecyloxy)phenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-5-methylthiazolium,hydroxide, inner salt

3-[3-[[[2-(Tetradecyloxy)phenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[3-[[[2-(Tetradecyloxy)-5-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[3-[[[2-(Tetradecyloxy)-5-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-5-methylthiazolium,hydroxide, inner salt

3-[3-[[[2-(Tetradecyloxy)-5-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[3-[[[2-(Tetradecyloxy)-5-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[3-[[[2-(Tetradecyloxy)-5-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-5-methylthiazolium,hydroxide, inner salt

3-[3-[[[2-(Tetradecyloxy)-5-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[3-[[[2-(Tetradecyloxy)-3-chlorophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[3-[[[2-(Tetradecyloxy)-3-chlorophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-5-methylthiazolium,hydroxide, inner salt

3-[3-[[[2-(Tetradecyloxy)-3-chlorophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[3-[[[2-(Dodecyloxy)phenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[3-[[[2-(Dodecyloxy)phenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[3-[[[2-(Dodecyloxy)-5-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[3-[[[2-(Dodecyloxy)-5-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[3-[[[2-(Dodecyloxy)-5-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[3-[[[2-(Dodecyloxy)-5-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[3-[[[2-(Dodecyloxy)-3-chlorophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[3-[[[2-(Dodecyloxy)-3-chlorophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[3-[[[4-(Hexadecyloxy)phenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[3-[[[4-(Hexadecyloxy)phenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-5-methylthiazolium,hydroxide, inner salt

3-[3-[[[4-(Hexadecyloxy)-2-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[3-[[[4-(Hexadecyloxy)-2-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-5-methylthiazolium,hydroxide, inner salt

3-[3-[[[4-(Hexadecyloxy)-2-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[3-[[[4-(Hexadecyloxy)-2-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-5-methylthiazolium,hydroxide, inner salt

3-[3-[[[4-(Hexadecyloxy)-2-nitrophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-5-methylthiazolium,hydroxide, inner salt

3-[3-[[[4-(Hexadecyloxy)-2-carbomethoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[3-[[[4-(Hexadecyloxy)-2,5-di-t-butylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[3-[[[4-(Hexadecyloxy)-2,5-di-t-butylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-5-methylthiazolium,hydroxide, inner salt

3-[3-[[[4-(Hexadecyloxy)-2,5-dichlorophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[3-[[[4-(Hexadecyloxy)-2,5-dichlorophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-5-methylthiazolium,hydroxide, inner salt

3-[3-[[[4-(Hexadecyloxy)-2-chlorophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[3-[[[4-(Hexadecyloxy)-2-chlorophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-5-methylthiazolium,hydroxide, inner salt

3-[3-[[[4-(Hexadecyloxy)-3-chlorophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-5-methylthiazolium,hydroxide, inner salt

3-[3-[[[4-(Tetradecyloxy)phenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[3-[[[4-(Tetradecyloxy)phenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-5-methylthiazolium,hydroxide, inner salt

3-[3-[[[4-(Tetradecyloxy)phenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[3-[[[4-(Tetradecyloxy)-2-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[3-[[[4-(Tetradecyloxy)-2-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-5-methylthiazolium,hydroxide, inner salt

3-[3-[[[4-(Tetradecyloxy)-2-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[3-[[[4-(Tetradecyloxy)-2-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[3-[[[4-(Tetradecyloxy)-2-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[3-[[[4-(Tetradecyloxy)-2-nitrophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[3-[[[4-(Tetradecyloxy)-2-nitrophenoxy]-hydroxyphosphinyl]oxy]phenyl]methyl]-5-methylthiazolium,hydroxide, inner salt

3-[3-[[[4-(Tetradecyloxy)-2-nitrophenoxy]hydroxphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[3-[[[4-(Tetradecyloxy)-2-carbomethoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[3-[[[4-(Tetradecyloxy)-2-carbomethoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-5-methylthiazolium,hydroxide, inner salt

3-[3-[[[4-(Tetradecyloxy)-2-carbomethoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[3-[[[4-(Tetradecyloxy)-2,5-di-t-butylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[3-[[[4-(Tetradecyloxy)-2,5-dichlorophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[3-[[[4-(Tetradecyloxy)-2,5-dichlorophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-5-methylthiazolium,hydroxide, inner salt

3-[3-[[[4-(Tetradecyloxy)-2,5-dichlorophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[3-[[[4-(Tetradecyloxy)-2-chlorophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[3-[[[4-(Tetaradecyloxy)-2-chlorophenoxy]hydroxyphosphinyl]oxy]-phenyl]methyl]-5-methylthiazolium,hydroxide, inner salt

3-[3-[[[4-(Tetradecyloxy)-2-chlorophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[3-[[[4-(Tetradecyloxy)-3-chlorophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[3-[[[4-(Tetradecyloxy)-3-chlorophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[3-[[[4-(Dodecyloxy)phenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[3-[[[4-(Dodecyloxy)phenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[3-[[[4-(Dodecyloxy)-2-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[3-[[[4-(Dodecyloxy)-2-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[3-[[[4-(Dodecyloxy)-2-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[3-[[[4-(Dodecyloxy)-2-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[3-[[[4-(Dodecyloxy)-2-nitrophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[3-[[[4-(Dodecyloxy)-2-nitrophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[3-[[[4-(Dodecyloxy)-2-carbomethoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[3-[[[4-(Dodecyloxy)-2,5-di-t-butylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[3-[[[4-(Dodecyloxy)-2,5-di-t-butylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[3-[[[4-(Dodecyloxy)-2,5-dichlorophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[3-[[[4-(Dodecyloxy)-2-chlorophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[3-[[[4-(Dodecyloxy)-2-chlorophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[3-[[[4-(Dodecyloxy)-3-chlorophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[3-[[[4-(Dodecyloxy)-3-chlorophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[2-[[[3-(Hexadecyloxy)phenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium, hydroxide, inner salt

3-[2-[[[3-(Hexadecyloxy)phenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-5-methylthiazolium,hydroxide, inner salt

3-[2-[[[3-(Hexadecyloxy)-2-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[2-[[[3-(Hexadecyloxy)-2-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-5-methylthiazolium,hydroxide, inner salt

3-[2-[[[3-(Hexadecyloxy)-2-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[2-[[[3-(Hexadecyloxy)-2-nitrophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[2-[[[3-(Hexadecyloxy)-2-nitrophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-5-methylthiazolium,hydroxide, inner salt

3-[2-[[[3-(Hexadecyloxy)-2-carbomethoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[2-[[[3-(Hexadecyloxy)-2-carbomethoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-5-methylthiazolium,hydroxide, inner salt

3-[2-[[[3-(Hexadecyloxy)-5-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[2-[[[3-(Hexadecyloxy)-5-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-5-methylthiazolium,hydroxide, inner salt

3-[2-[[[3-(Hexadecyloxy)-5-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[2-[[[3-(Hexadecyloxy)-5-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-5-methylthiazolium,hydroxide, inner salt

3-[2-[[[3-(Tetradecyloxy)phenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[2-[[[3-(Tetradecyloxy)phenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[2-[[[3-(Tetradecyloxy)-2-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[2-[[[3-(Tetradecyloxy)-2-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-5-methylthiazolium,hydroxide, inner salt

3-[2-[[[3-(Tetradecyloxy)-2-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[2-[[[3-(Tetradecyloxy)-2-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[2-[[[3-(Tetradecyloxy)-2-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-5-methylthiazolium,hydroxide, inner salt

3-[2-[[[3-(Tetradecyloxy)-2-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[2-[[[3-(Tetradecyloxy)-2-nitrophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[2-[[[3-(Tetradecyloxy)-2-nitrophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[2-[[[3-(Tetradecyloxy)-2-carbomethoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[2-[[[3-(Tetradecyloxy)-2-carbomethoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-5-methylthiazolium,hydroxide, inner salt

3-[2-[[[3-(Tetradecyloxy)-2-carbomethoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[2-[[[3-(Tetradecyloxy)-5-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[2-[[[3-(Tetradecyloxy)-5-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[2-[[[3-(Tetradecyloxy)-5-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[2-[[[3-(Tetradecyloxy)-5-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-5-methylthiazolium,hydroxide, inner salt

3-[2-[[[3-(Tetradecyloxy)-5-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[2-[[[3-(Dodecyloxy)phenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[2-[[[3-(Dodecyloxy)phenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[2-[[[3-(Dodecyloxy)-2-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[2-[[[3-(Dodecyloxy)-2-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[2-[[[3-(Dodecyloxy)-2-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[2-[[[3-(Dodecyloxy)-2-nitrophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[2-[[[3-(Dodecyloxy)-2-nitrophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[2-[[[3-(Dodecyloxy)-2-carbomethoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[2-[[[3-(Dodecyloxy)-2-carbomethoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[2-[[[3-(Dodecyloxy)-5-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[2-[[[3-(Dodecyloxy)-5-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[2-[[[3-(Dodecyloxy)-5-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[2-[[[2-(Hexadecyloxy)phenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[2-[[[2-(Hexadecyloxy)phenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-5-methylthiazolium,hydroxide, inner salt

3-[2-[[[2-(Hexadecyloxy)-5-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[2-[[[2-(Hexadecyloxy)-5-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-5-methylthiazolium,hydroxide, inner salt

3-[2-[[[2-(Hexadecyloxy)-5-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[2-[[[2-(Hexadecyloxy)-5-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-5-methylthiazolium,hydroxide, inner salt

3-[2-[[[2-(Hexadecyloxy)-3-chlorophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[2-[[[2-(Hexadecyloxy)-3-chlorophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-5-methylthiazolium,hydroxide, inner salt

3-[2-[[[2-(Tetradecyloxy)phenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[2-[[[2-(Tetradecyloxy)phenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[2-[[[2-(Tetradecyloxy)-5-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[2-[[[2-(Tetradecyloxy)-5-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-5-methylthiazolium,hydroxide, inner salt

3-[2-[[[2-(Tetradecyloxy)-5-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[2-[[[2-(Tetradecyloxy)-5-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[2-[[[2-(Tetradecyloxy)-5-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-5-methylthiazolium,hydroxide, inner salt

3-[2-[[[2-(Tetradecyloxy)-5-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[2-[[[2-(Tetradecyloxy)-3-chlorophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[2-[[[2-(Tetradecyloxy)-3-chlorophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[2-[[[2-(Dodecyloxy)phenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[2-[[[2-(Dodecyloxy)phenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[2-[[[2-(Dodecyloxy)-5-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[2-[[[2-(Dodecyloxy)-5-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[2-[[[2-(Dodecyloxy)-5-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[2-[[[2-(Dodecyloxy)-3-chlorophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[2-[[[2-(Dodecyloxy)-3-chlorophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[2-[[[4-(Hexadecyloxy)phenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[2-[[[4-(Hexadecyloxy)phenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-5-methylthiazolium,hydroxide, inner salt

3-[2-[[[4-(Hexadecyloxy)-2-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[2-[[[4-(Hexadecyloxy)-2-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-5-methylthiazolium,hydroxide, inner salt

3-[2-[[[4-(Hexadecyloxy)-2-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[2-[[[4-(Hexadecyloxy)-2-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-5-methylthiazolium,hydroxide, inner salt

3-[2-[[[4-(Hexadecyloxy)-2-nitrophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[2-[[[4-(Hexadecyloxy)-2-carbomethoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[2-[[[4-(Hexadecyloxy)-2-carbomethoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-5-methylthiazolium,hydroxide, inner salt

3-[2-[[[4-(Hexadecyloxy)-2,5-di-t-butylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[2-[[[4-(Hexadecyloxy)-2,5-di-t-butylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-5-methylthiazolium,hydroxide, inner salt

3-[2-[[[4-(Hexadecyloxy)-2,5-dichlorophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[2-[[[4-(Hexadecyloxy)-2-chlorophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[2-[[[4-(Hexadecyloxy)-2-chlorophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-5-methylthiazolium,hydroxide, inner salt

3-[2-[[[4-(Hexadecyloxy)-3-chlorophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[2-[[[4-(Hexadecyloxy)-3-chlorophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-5-methylthiazolium,hydroxide, inner salt

3-[2-[[[4-(Tetradecyloxy)phenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[2-[[[4-(Tetradecyloxy)phenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-5-methylthiazolium,hydroxide, inner salt

3-[2-[[[4-(Tetradecyloxy)phenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[2-[[[4-(Tetradecyloxy)-2-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[2-[[[4-(Tetradecyloxy)-2-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-5-methylthiazolium,hydroxide, inner salt

3-[2-[[[4-(Tetradecyloxy)-2-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[2-[[[4-(Tetradecyloxy)-2-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-5-methylthiazolium,hydroxide, inner salt

3-[2-[[[4-(Tetradecyloxy)-2-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[2-[[[4-(Tetradecyloxy)-2-nitrophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[2-[[[4-(Tetradecyloxy)-2-nitrophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-5-methylthiazolium,hydroxide, inner salt

3-[2-[[[4-(Tetradecyloxy)-2-nitrophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[2-[[[4-(Tetradecyloxy)-2-carbomethoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[2-[[[4-(Tetradecyloxy)-2-carbomethoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-5-methylthiazolium,hydroxide, inner salt

3-[2-[[[4-(Tetradecyloxy)-2-carbomethoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[2-[[[4-(Tetradecyloxy)-2,5-di-t-butylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[2-[[[4-(Tetradecyloxy)-2,5-di-t-butylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-5-methylthiazolium,hydroxide, inner salt

3-[2-[[[4-(Tetradecyloxy)-2,5-di-t-butylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[2-[[[4-(Tetradecyloxy)-2,5-dichlorophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[2-[[[4-(Tetradecyloxy)-2,5-dichlorophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[2-[[[4-(Tetradecyloxy)-2-chlorophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[2-[[[4-(Tetradecyloxy)-2-chlorophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-5-methylthiazolium,hydroxide, inner salt

3-[2-[[[4-(Tetradecyloxy)-2-chlorophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[2-[[[4-(Tetradecyloxy)-3-chlorophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[2-[[[4-(Tetradecyloxy)-3-chlorophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-5-methylthiazolium,hydroxide, inner salt

3-[2-[[[4-(Tetradecyloxy)-3-chlorophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[2-[[[4-(Dodecyloxy)phenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[2-[[[4-(Dodecyloxy)-2-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[2-[[[4-(Dodecyloxy)-2-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[2-[[[4-(Dodecyloxy)-2-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[2-[[[4-(Dodecyloxy)-2-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[2-[[[4-(Dodecyloxy)-2-nitrophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[2-[[[4-(Dodecyloxy)-2-carbomethoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[2-[[[4-(Dodecyloxy)-2-carbomethoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[2-[[[4-(Dodecyloxy)-2,5-di-t-butylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[2-[[[4-(Dodecyloxy)-2,5-di-t-butylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[2-[[[4-(Dodecyloxy)-2,5-dichlorophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[2-[[[4-(Dodecyloxy)-2,5-dichlorophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[2-[[[4-(Dodecyloxy)-2-chlorophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[2-[[[4-(Dodecyloxy)-2-chlorophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[2-[[[4-(Dodecyloxy)-3-chlorophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[2-[[[4-(Dodecyloxy)-3-chlorophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[4-[[[3-(Hexadecyloxy)phenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[4-[[[3-(Hexadecyloxy)phenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-5-methylthiazolium,hydroxide, inner salt

3-[4-[[[3-(Hexadecyloxy)-2-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[4-[[[3-(Hexadecyloxy)-2-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-5-methylthiazolium,hydroxide, inner salt

3-[4-[[[3-(Hexadecyloxy)-2-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[4-[[[3-(Hexadecyloxy)-2-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-5-methylthiazolium,hydroxide, inner salt

3-[4-[[[3-(Hexadecyloxy)-2-nitrophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[4-[[[3-(Hexadecyloxy)-2-nitrophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-5-methylthiazolium,hydroxide, inner salt

3-[4-[[[3-(Hexadecyloxy)-2-carbomethoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[4-[[[3-(Hexadecyloxy)-5-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[4-[[[3-(Hexadecyloxy)-5-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-5-methylthiazolium,hydroxide, inner salt

3-[4-[[[3-(Hexadecyloxy)-5-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[4-[[[3-(Hexadecyloxy)-5-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-5-methylthiazolium,hydroxide, inner salt

3-[4-[[[3-(Tetradecyloxy)phenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[4-[[[3-(Tetradecyloxy)phenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-5-methylthiazolium,hydroxide, inner salt

3-[4-[[[3-(Tetradecyloxy)phenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[4-[[[3-(Tetradecyloxy)-2-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[4-[[[3-(Tetradecyloxy)-2-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[4-[[[3-(Tetradecyloxy)-2-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[4-[[[3-(Tetradecyloxy)-2-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-5-methylthiazolium,hydroxide, inner salt

3-[4-[[[3-(Tetradecyloxy)-2-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[4-[[[3-(Tetradecyloxy)-2-nitrophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[4-[[[3-(Tetradecyloxy)-2-nitrophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-5-methylthiazolium,hydroxide, inner salt

3-[4-[[[3-(Tetradecyloxy)-2-carbomethoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[4-[[[3-(Tetradecyloxy)-2-carbomethoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-5-methylthiazolium,hydroxide, inner salt

3-[4-[[[3-(Tetradecyloxy)-2-carbomethoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[4-[[[3-(Tetradecyloxy)-5-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[4-[[[3-(Tetradecyloxy)-5-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-5-methylthiazolium,hydroxide, inner salt

3-[4-[[[3-(Tetradecyloxy)-5-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[4-[[[3-(Tetradecyloxy)-5-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[4-[[[3-(Tetradecyloxy)-5-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-5-methylthiazolium,hydroxide, inner salt

3-[4-[[[3-(Dodecyloxy)phenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[4-[[[3-(Dodecyloxy)phenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[4-[[[3-(Dodecyloxy)-2-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[4-[[[3-(Dodecyloxy)-2-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[4-[[[3-(Dodecyloxy)-2-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[4-[[[3-(Dodecyloxy)-2-nitrophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[4-[[[3-(Dodecyloxy)-2-nitrophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[4-[[[3-(Dodecyloxy)-2-carbomethoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[4-[[[3-(Dodecyloxy)-2-carbomethoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[4-[[[3-(Dodecyloxy)-5-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[4-[[[3-(Dodecyloxy)-5-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[4-[[[3-(Dodecyloxy)-5-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[4-[[[3-(Dodecyloxy)-5-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[4-[[[2-(Hexadecyloxy)phenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[4-[[[2-(Hexadecyloxy)-5-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[4-[[[2-(Hexadecyloxy)-5-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-5-methylthiazolium,hydroxide, inner salt

3-[4-[[[2-(Hexadecyloxy)-5-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[4-[[[2-(Hexadecyloxy)-5-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-5-methylthiazolium,hydroxide, inner salt

3-[4-[[[2-(Hexadecyloxy)-3-chlorophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[4-[[[2-(Hexadecyloxy)-3-chlorophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-5-methylthiazolium,hydroxide, inner salt

3-[4-[[[2-(Tetradecyloxy)phenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[4-[[[2-(Tetradecyloxy)phenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[4-[[[2-(Tetradecyloxy)-5-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[4-[[[2-(Tetradecyloxy)-5-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[4-[[[2-(Tetradecyloxy)-5-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[4-[[[2-(Tetradecyloxy)-5-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-5-methylthiazolium,hydroxide, inner salt

3-[4-[[[2-(Tetradecyloxy)-5-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[4-[[[2-(Tetradecyloxy)-3-chlorophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[4-[[[2-(Tetradecyloxy)-3-chlorophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[4-[[[2-(Dodecyloxy)phenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[4-[[[2-(Dodecyloxy)phenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[4-[[[2-(Dodecyloxy)-5-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[4-[[[2-(Dodecyloxy)-5-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[4-[[[2-(Dodecyloxy)-5-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[4-[[[2-(Dodecyloxy)-5-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[4-[[[2-(Dodecyloxy)-3-chlorophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[4-[[[4-(Hexadecyloxy)phenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[4-[[[4-(Hexadecyloxy)phenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-5-methylthiazolium,hydroxide, inner salt

3-[4-[[[4-(Hexadecyloxy)-2-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[4-[[[4-(Hexadecyloxy)-2-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-5-methylthiazolium,hydroxide, inner salt

3-[4-[[[4-(Hexadecyloxy)-2-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[4-[[[4-(Hexadecyloxy)-2-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-5-methylthiazolium,hydroxide, inner salt

3-[4-[[[4-(Hexadecyloxy)-2-nitrophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[4-[[[4-(Hexadecyloxy)-2-carbomethoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[4-[[[4-(Hexadecyloxy)-2-carbomethoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-5-methylthiazolium,hydroxide, inner salt

3-[4-[[[4-(Hexadecyloxy)-2,5-di-t-butylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[4-[[[4-(Hexadecyloxy)-2,5-di-t-butylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-5-methylthiazolium,hydroxide, inner salt

3-[4-[[[4-(Hexadecyloxy)-2,5-dichlorophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[4-[[[4-(Hexadecyloxy)-2,5-dichlorophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-5-methylthiazolium,hydroxide, inner salt

3-[4-[[[4-(Hexadecyloxy)-2-chlorophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[4-[[[4-(Hexadecyloxy)-3-chlorophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[4-[[[4-(Tetradecyloxy)phenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[4-[[[4-(Tetradecyloxy)phenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-5-methylthiazolium,hydroxide, inner salt

3-[4-[[[4-(Tetradecyloxy)phenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[4-[[[4-(Tetradecyloxy)-2-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[4-[[[4-(Tetradecyloxy)-2-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-5-methylthiazolium,hydroxide, inner salt

3-[4-[[[4-(Tetradecyloxy)-2-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[4-[[[4-(Tetradecyloxy)-2-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[4-[[[4-(Tetradecyloxy)-2-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-5-methylthiazolium,hydroxide, inner salt

3-[4-[[[4-(Tetradecyloxy)-2-nitrophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[4-[[[4-(Tetradecyloxy)-2-nitrophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-5-methylthiazolium,hydroxide, inner salt

3-[4-[[[4-(Tetradecyloxy)-2-nitrophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[4-[[[4-(Tetradecyloxy)-2-carbomethoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[4-[[[4-(Tetradecyloxy)-2-carbomethoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-5-methylthiazolium,hydroxide, inner salt

3-[4-[[[4-(Tetradecyloxy)-2-carbomethoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[4-[[[4-(Tetradecyloxy)-2,5-di-t-butylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[4-[[[4-(Tetradecyloxy)-2,5-di-t-butylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[4-[[[4-(Tetradecyloxy)-2,5-dichlorophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[4-[[[4-(Tetradecyloxy)-2,5-dichlorophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-5-methylthiazolium,hydroxide, inner salt

3-[4-[[[4-(Tetradecyloxy)-2,5-dichlorophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[4-[[[4-(Tetradecyloxy)-2-chlorophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[4-[[[4-(Tetradecyloxy)-2-chlorophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-5-methylthiazolium,hydroxide, inner salt

3-[4-[[[4-(Tetradecyloxy)-3-chlorophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[4-[[[4-(Tetradecyloxy)-3-chlorophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[4-[[[4-(Dodecyloxy)phenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[4-[[[4-(Dodecyloxy)phenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[4-[[[4-(Dodecyloxy)-2-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[4-[[[4-(Dodecyloxy)-2-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[4-[[[4-(Dodecyloxy)-2-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[4-[[[4-(Dodecyloxy)-2-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[4-[[[4-(Dodecyloxy)-2-nitrophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[4-[[[4-(Dodecyloxy)-2-carbomethoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[4-[[[4-(Dodecyloxy)-2-carbomethoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[4-[[[4-(Dodecyloxy)-2,5-di-t-butylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[4-[[[4-(Dodecyloxy)-2,5-di-t-butylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[4-[[[4-(Dodecyloxy)-2,5-dichlorophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[4-[[[4-(Dodecyloxy)-2,5-dichlorophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

3-[4-[[[4-(Dodecyloxy)-2-chlorophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[4-[[[4-(Dodecyloxy)-3-chlorophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[4-[[[4-(Dodecyloxy)-3-chlorophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-4-methylthiazolium,hydroxide, inner salt

1-[3-[[[3-(Hexadecyloxy)phenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

1-[3-[[[3-(Hexadecyloxy)-2-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

1-[3-[[[3-(Hexadecyloxy)-2-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

1-[3-[[[3-(Hexadecyloxy)-2-nitrophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

1-[3-[[[3-(Hexadecyloxy)-2-carbomethoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

1-[3-[[[3-(Hexadecyloxy)-5-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

1-[3-[[[3-(Tetradecyloxy)-2-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]pyridinium,hydroxide, inner salt

1-[3-[[[3-(Tetradecyloxy)-2-nitrophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]pyridinium,hydroxide, inner salt

1-[3-[[[3-(Tetradecyloxy)-2-carbomethoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]pyridinium,hydroxide, inner salt

1-[3-[[[3-(Tetradecyloxy)-5-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]pyridinium,hydroxide, inner salt

1-[3-[[[3-(Tetradecyloxy)-5-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]pyridinium,hydroxide, inner salt

1-[3-[[[3-(Dodecyloxy)phenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

1-[3-[[[3-(Dodecyloxy)-2-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

1-[3-[[[3-(Dodecyloxy)-2-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

1-[3-[[[3-(Dodecyloxy)-2-carbomethoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

1-[3-[[[3-(Dodecyloxy)-5-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

1-[3-[[[3-(Dodecyloxy)-5-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

1-[3-[[[2-(Hexadecyloxy)phenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

1-[3-[[[2-(Hexadecyloxy)-5-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

1-[3-[[[2-(Hexadecyloxy)-5-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

1-[3-[[[2-(Hexadecyloxy)-3-chlorophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

1-[3-[[[2-(Tetradecyloxy)phenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]pyridinium,hydroxide, inner salt

1-[3-[[[2-(Tetradecyloxy)-5-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]pyridinium,hydroxide, inner salt

1-[3-[[[2-(Tetradecyloxy)-3-chlorophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]pyridinium,hydroxide, inner salt

1-[3-[[[2-(Dodecyloxy)phenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

1-[3-[[[2-(Dodecyloxy)-5-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

1-[3-[[[2-(Dodecyloxy)-5-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

1-[3-[[[2-(Dodecyloxy)-3-chlorophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

1-[3-[[[4-(Hexadecyloxy)phenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

1-[3-[[[4-(Hexadecyloxy)-2-nitrophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

1-[3-[[[4-(Hexadecyloxy)-2-carbomethoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

1-[3-[[[4-(Hexadecyloxy)-2,5-di-t-butylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

1-[3-[[[4-(Hexadecyloxy)-2,5-dichlorophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

1-[3-[[[4-(Hexadecyloxy)-2-chlorophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

1-[3-[[[4-(Tetradecyloxy)phenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]pyridinium,hydroxide, inner salt

1-[3-[[[4-(Tetradecyloxy)-2-nitrophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]pyridinium,hydroxide, inner salt

1-[3-[[[4-(Tetradecyloxy)-2-carbomethoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]pyridinium,hydroxide, inner salt

1-[3-[[[4-(Tetradecyloxy)-2,5-di-t-butylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]pyridinium,hydroxide, inner salt

1-[3-[[[4-(Tetradecyloxy)-2,5-dichlorophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]pyridinium,hydroxide, inner salt

1-[3-[[[4-(Tetradecyloxy)-2-chlorophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]pyridinium,hydroxide, inner salt

1-[3-[[[4-(Tetradecyloxy)-3-chlorophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]pyridinium,hydroxide, inner salt

1-[3-[[[4-(Dodecyloxy)phenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

1-[3-[[[4-(Dodecyloxy)-2-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

1-[3-[[[4-(Dodecyloxy)-2-carbomethoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

1-[3-[[[4-(Dodecyloxy)-2,5-di-t-butylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

1-[3-[[[4-(Dodecyloxy)-2,5-dichlorophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

1-[3-[[[4-(Dodecyloxy)-2-chlorophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

1-[3-[[[4-(Dodecyloxy)-3-chlorophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

1-[2-[[[3-(Hexadecyloxy)phenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

1-[2-[[[3-(Hexadecyloxy)-2-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

1-[2-[[[3-(Hexadecyloxy)-2-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

1-[2-[[[3-(Hexadecyloxy)-5-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

1-[2-[[[3-(Hexadecyloxy)-5-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

1-[2-[[[3-(Tetradecyloxy)phenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]pyridinium,hydroxide, inner salt

1-[2-[[[3-(Tetradecyloxy)-2-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]pyridinium,hydroxide, inner salt

1-[2-[[[3-(Tetradecyloxy)-2-nitrophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]pyridinium,hydroxide, inner salt

1-[2-[[[3-(Tetradecyloxy)-2-carbomethoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]pyridinium,hydroxide, inner salt

1-[2-[[[3-(Tetradecyloxy)-5-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]pyridinium,hydroxide, inner salt

1-[2-[[[3-(Dodecyloxy)phenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

1-[2-[[[3-(Dodecyloxy)-2-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

1-[2-[[[3-(Dodecyloxy)-2-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

1-[2-[[[3-(Dodecyloxy)-2-nitrophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

1-[2-[[[3-(Dodecyloxy)-2-carbomethoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

1-[2-[[[3-(Dodecyloxy)-5-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

1-[2-[[[2-(Hexadecyloxy)phenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

1-[2-[[[2-(Hexadecyloxy)-5-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

1-[2-[[[2-(Hexadecyloxy)-5-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

1-[2-[[[2-(Hexadecyloxy)-3-chlorophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

1-[2-[[[2-(Tetradecyloxy)phenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]pyridinium,hydroxide, inner salt

1-[2-[[[2-(Dodecyloxy)phenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

1-[2-[[[2-(Dodecyloxy)-5-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

1-[2-[[[2-(Dodecyloxy)-5-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

1-[2-[[[2-(Dodecyloxy)-3-chlorophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

1-[2-[[[4-(Hexadecyloxy)phenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

1-[2-[[[4-(Hexadecyloxy)-2-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

1-[2-[[[4-(Hexadecyloxy)-2-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

1-[2-[[[4-(Hexadecyloxy)-2-nitrophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

1-[2-[[[4-(Hexadecyloxy)-2-carbomethoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

1-[2-[[[4-(Hexadecyloxy)-2,5-di-t-butylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

1-[2-[[[4-(Hexadecyloxy)-2,5-dichlorophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

1-[2-[[[4-(Hexadecyloxy)-3-chlorophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

1-[2-[[[4-(Tetradecyloxy)phenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]pyridinium,hydroxide, inner salt

1-[2-[[[4-(Tetradecyloxy)-2-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]pyridinium,hydroxide, inner salt

1-[2-[[[4-(Tetradecyloxy)-2-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]pyridinium,hydroxide, inner salt

1-[2-[[[4-(Tetradecyloxy)-2-nitrophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]pyridinium,hydroxide, inner salt

1-[2-[[[4-(Tetradecyloxy)-3-chlorophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]pyridinium,hydroxide, inner salt

1-[2-[[[4-(Dodecyloxy)phenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

1-[2-[[[4-(Dodecyloxy)-2-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

1-[2-[[[4-(Dodecyloxy)-2-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

1-[2-[[[4-(Dodecyloxy)-2-nitrophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

1-[2-[[[4-(Dodecyloxy)-2-carbomethoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium, hydroxide, inner salt

1-[2-[[[4-(Dodecyloxy)-2,5-di-t-butylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

1-[2-[[[4-(Dodecyloxy)-2,5-dichlorophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

1-[2-[[[4-(Dodecyloxy)-2-chlorophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

1-[2-[[[4-(Dodecyloxy)-3-chlorophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

1-[4-[[[3-(Hexadecyloxy)-2-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

1-[4-[[[3-(Hexadecyloxy)-2-nitrophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

1-[4-[[[3-(Hexadecyloxy)-2-carbomethoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

1-[4-[[[3-(Hexadecyloxy)-5-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

1-[4-[[[3-(Hexadecyloxy)-5-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

1-[4-[[[3-(Tetradecyloxy)-2-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]pyridinium,hydroxide, inner salt

1-[4-[[[3-(Tetradecyloxy)-2-nitrophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]pyridinium,hydroxide, inner salt

1-[4-[[[3-(Tetradecyloxy)-2-carbomethoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]pyridinium,hydroxide, inner salt

1-[4-[[[3-(Tetradecyloxy)-5-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]pyridinium,hydroxide, inner salt

1-[4-[[[3-(Tetradecyloxy)-5-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]pyridinium,hydroxide, inner salt

1-[4-[[[3-(Dodecyloxy)phenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

1-[4-[[[3-(Dodecyloxy)-2-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

1-[4-[[[3-(Dodecyloxy)-2-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

1-[4-[[[3-(Dodecyloxy)-2-nitrophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

1-[4-[[[3-(Dodecyloxy)-2-carbomethoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

1-[4-[[[3-(Dodecyloxy)-5-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

1-[4-[[[2-(Hexadecyloxy)phenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

1-[4-[[[2-(Hexadecyloxy)-5-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

1-[4-[[[2-(Hexadecyloxy)-5-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

1-[4-[[[2-(Hexadecyloxy)-3-chlorophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

1-[4-[[[2-(Tetradecyloxy)phenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]pyridinium,hydroxide, inner salt

1-[4-[[[2-(Tetradecyloxy)-5-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]pyridinium,hydroxide, inner salt

1-[4-[[[2-(Tetradecyloxy)-3-chlorophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]pyridinium,hydroxide, inner salt

1-[4-[[[2-(Dodecyloxy)phenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

1-[4-[[[2-(Dodecyloxy)-5-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

1-[4-[[[2-(Dodecyloxy)-5-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

1-[4-[[[2-(Dodecyloxy)-3-chlorophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

1-[4-[[[4-(Hexadecyloxy)phenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

1-[4-[[[4-(Hexadecyloxy)-2-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

1-[4-[[[4-(Hexadecyloxy)-2-nitrophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

1-[4-[[[4-(Hexadecyloxy)-2-carbomethoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

1-[4-[[[4-(Hexadecyloxy)-2,5-di-t-butylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

1-[4-[[[4-(Hexadecyloxy)-2,5-dichlorophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

1-[4-[[[4-(Hexadecyloxy)-2-chlorophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

1-[4-[[[4-(Tetradecyloxy)-2-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]pyridinium,hydroxide, inner salt

1-[4-[[[4-(Tetradecyloxy)-2-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]pyridinium,hydroxide, inner salt

1-[4-[[[4-(Tetradecyloxy)-2-nitrophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]pyridinium,hydroxide, inner salt

1-[4-[[[4-(Tetradecyloxy)-2-carbomethoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]pyridinium,hydroxide, inner salt

1-[4-[[[4-(Tetradecyloxy)-2,5-di-t-butylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]pyridinium,hydroxide, inner salt

1-[4-[[[4-(Tetradecyloxy)-2,5-dichlorophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]pyridinium,hydroxide, inner salt

1-[4-[[[4-(Tetradecyloxy)-2-chlorophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]pyridinium,hydroxide, inner salt

1-[4-[[[4-(Dodecyloxy)-2-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

1-[4-[[[4-(Dodecyloxy)-2-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

1-[4-[[[4-(Dodecyloxy)-2-nitrophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

1-[4-[[[4-(Dodecyloxy)-2-carbomethoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

1-[4-[[[4-(Dodecyloxy)-2,5-di-t-butylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

1-[4-[[[4-(Dodecyloxy)-2,5-dichlorophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

1-[4-[[[4-(Dodecyloxy)-2-chlorophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]quinolinium,hydroxide, inner salt

3-[[3-[[[[6-(Dodecyloxy)-2-naphthalenyl]oxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[[3-[[[[4-(Dodecyloxy)-1-naphthalenyl]oxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[[3-[[[[3-(Dodecyloxy)-2-naphthalenyl]oxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[[3-[[[[5-(Dodecyloxy)-1-naphthalenyl]oxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium, hydroxide, inner salt

3-[[3-[[[[8-(Dodecyloxy)-1-naphthalenyl]oxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

3-[[3-[[[[7-(Tetradecyloxy)-2-naphthalenyl]oxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt

In addition to the utilities described hereinabove, many of thecompounds of this invention are useful as precursors to other compoundsof this invention.

We claim:
 1. A compound of the formula: ##STR12## wherein: X is a phenylor napthyl ring optionally substituted in any position with one to fivesubstituents on the phenyl group and one to seven substituents on thenaphthyl group of;(i) --R₂, wherein R₂ is C₁ -C₂₅ alkyl, C₁ -C₂₅alkenyl, C₁ -C₂₅ alkoxy, C₁ -C₂₅ thioalkyl, C₁ -C₂₅ alkenyloxy, phenyl,phenoxy, substituted phenyl or substituted phenoxy wherein thesubstituted are C₁ -C₂₀ alkyl, C₁ -C₂₀ alkoxy, halogen ortrifluoromethyl; (ii) hydrogen, halogen, trifluoromethyl, cyano andnitro; (iii) --CO₂ R₃, --CONHR₃, --CHO, OCONHR₃, and --NHCOR₃ wherein R₃is C₁ -C₂₅ alkyl, C₁ -C₂₅ alkenyl, phenyl or substituted phenyl whereinthe substituents are C₁ -C₂₀ alkyl, C₁ -C₂₀ alkoxy, halogen ortrifluoromethyl; R₁ is one or more substituents of the aromatic ringwhich may be in any position and are hydrogen, C₁ -C₅ alkyl, C₁ -C₅alkoxy or halogen; --CH₂ --Y is a single substituent of the aromaticring which may occupy any position wherein Y is ##STR13## wherein R₄represents one or more substituents of the heterocyclic ring which mayoccupy a non-hetero atom position and is C₁ -C₅ alkyl, C₁ -C₅ alkoxy,hydrogen or halogen; the moiety R₅ is C₁ -C₅ alkyl or hydrogen; and; nis the integer 0 to
 1. 2. A compound according to claim 1 wherein n=o.3. The compound according to claim 1 wherein R₁ is hydrogen.
 4. Thecompound according to claim 3,3-[[2-[[[3-(hexadecyloxy)phenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt.
 5. The compound according to claim 1,3-[[3-[[hydroxy[[3-(tetradecyloxy)phenyl]methoxy]phosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt.
 6. The compound according to claim 3,3-[[3-[[[3-(hexadecyloxy)phenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt.
 7. The compound according to claim 3,3-[[3-[[[3-(hexadecyloxy)-2-methylphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt.
 8. The compound according to claim 3,3-[[3-[[hydroxy[2-methoxy-3-(tetradecyloxy)phenoxy]phosphinyl]oxy]phenyl]methyl]-5-methyl-thiazolium,hydroxide, inner salt.
 9. The compound according to claim 3,3-[[3-[[hydroxy[2-(tetradecyloxy)phenoxy]phosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt.
 10. The compound according to claim 3,3-[[3-[[hydroxy(3-tetradecylphenoxy)phosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt.
 11. The compound according to claim 3,3-[[3-[[hydroxy[2-methoxy-3-(tetradecyloxy)phenoxy]phosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt.
 12. The compound according to claim 3,3-[[3-[[[3-(dodecyloxy)phenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt.
 13. The compound according to claim 3,3-[[3-[[[[7-(dodecyloxy)-2-naphthalenyl]oxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt.
 14. The compound according to claim 3,3-[[3-[[hydroxy[2-(methoxycarbonyl)-3-(tetradecyloxy)phenoxy]phosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt.
 15. The compound according to claim 3,3-[[3-[[hydroxy[2-(methoxycarbonyl)-3-(tetradecyloxy)phenoxy]phosphinyl]oxy]phenyl]methyl]-5-methyl-thiazolium,hydroxide, inner salt.
 16. The compound according to claim 3,3-[[3-[[[2,4-bis(1,1-dimethylethyl)-5-(dodecyloxy)phenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt.
 17. The compound according to claim 3,3-[[2-[[[2,5-bis(1,1-dimethylethyl)-4-(dodecyloxy)phenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-5-methyl-thiazolium,hydroxide, inner salt.
 18. The compound according to claim 3,3-[[3-[[[2,5-bis(1,1-dimethylethyl)-4-(dodecyloxy)phenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt.
 19. The compound according to claim 3,3-[[3-[[hydroxy[3-(tetradecyloxy)phenoxy]phosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt.
 20. The compound according to claim 3,3-[[3-[[hydroxy[3-(tetradecyloxy)phenoxy]phosphinyl]oxy]phenyl]methyl]-5-methyl-thiazolium,hydroxide, inner salt.
 21. The compound according to claim 3,3-[[3-[[3-[4-(hexadecyloxy)phenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt.
 22. The compound according to claim 3,3-[[3-[hydroxy[3-(tetradecyloxy)phenoxy]phosphinyl]oxy]phenyl]methyl]-5-methyl-thiazolium,hydroxide, inner salt.
 23. The compound according to claim 3,3-[[3-[[hydroxy(3-tetradecylphenoxy)phosphinyl]oxy]phenyl]methyl]-thiazolium,hydroxide, inner salt.
 24. The compound according to claim 3,3-[[3-[[[2,5-bis(1,1-dimethylethyl)-4-(dodecyloxy)phenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-5-methyl-thiazolium,hydroxide, inner salt.
 25. The compound according to claim 3,3-[[3-[[hydroxy[4-(phenylmethoxy)phenoxy]phosphinyl]oxy]phenyl]methyl]-5-methylthiazolium, hydroxide, inner salt.
 26. The compound according to claim3,3-[[3-[[[(1,1-biphenyl)-3-yloxy]hydroxyphosphinyl]oxy]phenylmethyl]thiazolium,hydroxide, inner salt.
 27. The compound according to claim 3,3-[[3-[[(3-chlorophenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt.
 28. The compound according to claim 3,3-[[3-[[2-chlorophenoxy)hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt.
 29. The compound according to claim 3,3-[[3-[[(4-chlorophenoxy)hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt.
 30. The compound according to claim 3,3-[[3-[[[3-(dodecyloxy)-2-methoxyphenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt.
 31. The compound according to claim 3,3-[[3-[[hydroxy[2-methyl-3-[[(octadecylamino]carbonyl]oxy]phenoxy]phosphinyl]oxy]phenyl]methyl]-5-methyl-thiazolium,hydroxide, inner salt.
 32. The compound according to claim 3,3-[[3-[[hydroxy[2-methyl-3-[[(octadecylamino)carbonyl]oxy]phenoxy]phosphinyl]oxy]phenyl]methyl]-thiazolium,hydroxide, inner salt.
 33. The compound according to claim 2,3-[[3-[[[2,5-dichloro-4-(tetradecyloxy)phenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]-5-methyl-thiazolium,hydroxide, inner salt.
 34. The compound according to claim 3,3-[[3-[[[2,5-bis(1,1-dimethylethyl)-4-[[(octadecylamino)carbonyl]oxy]phenoxy]hydroxyphosphinyl]oxy]phenyl]methyl]thiazolium,hydroxide, inner salt.
 35. A composition of matter in dosage unit formwhich comprises a compound of claim 1 in association with apharmaceutically acceptable carrier.